Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives

ABSTRACT

The invention relates to novel compounds of the formula (I) 
                         
in which
     W, X, Y, Z, A and G have the meanings given above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising, firstly, the cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives of the formula (I) and, secondly, at least one crop plant compatibility-improving compound.   

     The invention relates furthermore to increasing the activity of crop protection compositions comprising compounds of the formula (I) by adding ammonium or phosphonium salts and, if appropriate, penetrants.

The present invention relates to novel cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives, to a plurality ofprocesses for their preparation and to their use as pesticides and/orherbicides. The invention also provides selective herbicidalcompositions comprising, firstly, the cis-alkoxy-spirocyclicbiphenyl-substituted tetramic acid derivatives and, secondly, a cropplant compatibility-improving compound.

The present invention further relates to the boosting of the action ofcrop protection compositions comprising, in particular,cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives,through the addition of ammonium salts or phosphonium salts andoptionally penetrants, to the corresponding compositions, to processesfor producing them and to their application in crop protection asinsecticides and/or acaricides and/or for preventing unwanted plantgrowth.

For 3-acylpyrrolidine-2,4-diones pharmaceutical properties have beenpreviously described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have beensynthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem.1985, 1095). Biological activity of these compounds has not beendescribed.

EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structuredcompounds (3-arylpyrrolidine-2,4-diones) for which, however, noherbicidal, insecticidal or acaricidal action has been disclosed. Knowncompounds with herbicidal, insecticidal or acaricidal action areunsubstituted bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355599, EP-A-415 211 and JP-A-12-053 670) and also substituted monocyclic3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A 442 077).

Additionally known are polycyclic 3-arylpyrrolidine-2,4-dionederivatives (EP-A-442 073) and also 1H-arylpyrrolidinedione derivatives(EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A 613 884, EP-A-613 885,WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395,WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO99/43649, WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO01/74770, WO 03/013249, WO 04/007448, WO 04/024688, WO 04/065366, WO04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO05/049596, WO 05/066125, WO 05/092897, WO 06/000355, WO 06/029799, WO06/056281, WO 06/056282, WO 06/089633, WO 07/048545, WO 07/073856,DE-A-05/059892, DE-A-06/007882, DE-A-06/018828, DE-A-06/025874,DE-A-06/050148).

Also known are biphenyl-substituted 1H-pyrrolidinedione derivativeshaving fungicidal action (WO 03/059065).

However, in particular at low application rates and concentrations, theactivity and activity spectrum of these compounds is not alwayssatisfactory. Furthermore, the compatibility of these compounds withsome crop plants is not always sufficient. Moreover, the toxicologicalproperties and/or environmental properties of these compounds are notalways entirely satisfactory.

This invention now provides novel compounds of the formula (I)

in which

-   X represents halogen, alkyl, alkoxy, haloalkyl or haloalkoxy,-   Z represents optionally mono- or polysubstituted fluorophenyl,-   W and Y independently of one another represent hydrogen, halogen,    alkyl, alkoxy, haloalkyl or haloalkoxy,-   A represents alkyl,-   G represents hydrogen (a) or represents one of the groups

in which

-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulphur,-   M represents oxygen or sulphur,-   R¹ represents in each case optionally halogen-substituted alkyl,    alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally    halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be    interrupted by at least one heteroatom, in each case optionally    substituted phenyl, phenylalkyl, hetaryl phenoxyalkyl or    hetaryloxyalkyl,-   R² represents in each case optionally halogen-substituted alkyl,    alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case    optionally substituted cycloalkyl, phenyl or benzyl,-   R³, R⁴ and R⁵ independently of one another represent in each case    optionally halogen-substituted alkyl, alkoxy, alkylamino,    dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent in    each case optionally substituted phenyl, benzyl, phenoxy or    phenylthio and-   R⁶ and R⁷ independently of one another represent hydrogen, in each    case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,    alkoxy, alkoxyalkyl, represent optionally substituted phenyl,    represent optionally substituted benzyl or together with the    nitrogen atom to which they are attached represent a ring which is    optionally interrupted by oxygen or sulphur.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) may be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if appropriate, may beseparated in a customary manner. The present invention provides for thepure isomers and the isomer mixtures, their preparation and use andcompositions comprising them. However, for the sake of simplicity,hereinbelow only compounds of the formula (I) are referred to, althoughwhat is meant are both the pure compounds and, if appropriate, mixtureshaving various proportions of isomeric compounds.

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) ofgroup G, the following principal structures (I-a) to (I-g) (cis-isomer)result:

in whichA, E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the meaningsgiven above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

-   (A) Compounds of the formula (I-a),

-   -   in which    -   A, W, X, Y and Z have the meanings given above,    -   are obtained when    -   compounds of the formula (II),

-   -   in which    -   A, W, X, Y and Z have the meanings given above,    -   and    -   R⁸ represents alkyl (preferably C₁-C₆-alkyl),    -   are condensed intramolecularly in the presence of diluent and in        the presence of a base.

-   (B) Furthermore, it has been found that compounds of the formulae    (I-a) to (I-g) shown above, in which A, G, W, X, Y and Z have the    meaning given above, are obtained when compounds of the formulae    (I-a′) to (I-g′),

-   -   in which    -   W, X and Y have the meaning given above and    -   Z′ represents chlorine, bromine, iodine, preferably bromine,    -   are reacted with boronic acids or boronic acid derivatives of        the formula (III)

-   -   in which    -   R⁹ represents hydrogen, C₁-C₆-alkyl or C₂-C₆-alkanediyl    -   and    -   Z has the meaning given above,    -   in the presence of a solvent, a base and a catalyst, suitable        catalysts being in particular palladium salts or palladium        complexes.    -   Moreover, it has been found

-   (C) that the compounds of the formula (I-b) shown above, in which A,    R¹, W, X, Y and Z have the meanings given above, are obtained when    compounds of the formula (I-a) shown above, in which A, W, X, Y and    Z have the meanings given above, are in each case    -   (α) reacted with acid halides of the formula (IV)

-   -   in which    -   R¹ has the meaning given above and    -   Hal represents halogen (in particular chlorine or bromine)    -   or    -   (β) reacted with carboxylic anhydrides of the formula (V)        R¹—CO—O—CO—R¹  (V)    -   in which    -   R¹ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (D) that the compounds of the formula (I-c) shown above, in which A,    R², M, W, X, Y and Z have the meanings given above and L represents    oxygen, are obtained when compounds of the formula (I-a) shown    above, in which A, W, X, Y and Z have the meanings given above, are    in each case    -   reacted with chloroformic esters or chloroformic thioesters of        the formula (VI)        R²-M-CO—Cl  (VI)    -   in which    -   R² and M have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (E) that compounds of the formula (I-c) shown above, in which A, R²,    M, W, X, Y and Z have the meanings given above and L represents    sulphur, are obtained when compounds of the formula (I-a) shown    above, in which A, W, X, Y and Z have the meanings given above, are    in each case    -   reacted with chloromonothioformic esters or chlorodithioformic        esters of the formula (VII)

-   -   in which    -   M and R² have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,    -   and

-   (F) that compounds of the formula (I-d) shown above, in which A, R³,    W, X, Y and Z have the meanings given above, are obtained when    compounds of the formula (I-a) shown above, in which A, W, X, Y and    Z have the meanings given above, are in each case    -   reacted with sulphonyl chlorides of the formula (VIII)        R³—SO₂—Cl  (VIII)    -   in which    -   R³ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formula (I-e) shown above, in which A, L,    R⁴, R⁵, W, X, Y and Z have the meanings given above, are obtained    when compounds of the formula (I-a) shown above, in which A, W, X, Y    and Z have the meanings given above are in each case    -   reacted with phosphorus compounds of the formula (IX)

-   -   in which    -   L, R⁴ and R⁵ have the meanings given above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (H) that compounds of the formula (I-f) shown above, in which A, E,    W, X, Y and Z have the meanings given above, are obtained when    compounds of the formula (I-a) shown above, in which A, W, X, Y and    Z have the meanings given above, are in each case    -   reacted with metal compounds or amines of the formulae (X) or        (XI), respectively,

-   -   in which    -   Me represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal, such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or        alkyl (preferably C₁-C₈-alkyl),    -   if appropriate in the presence of a diluent,

-   (I) that compounds of the formula (I-g) shown above, in which A, L,    R⁶, R⁷, W, X, Y and Z have the meanings given above, are obtained    when compounds of the formula (I-a) shown above, in which A, W, X, Y    and Z have the meanings given above, are in each case    -   (α) reacted with isocyanates or isothiocyanates of the formula        (XII)        R⁶—N═C=L  (XII)    -   in which    -   R⁶ and L have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or    -   (β) reacted with carbamoyl chlorides or thiocarbamoyl chlorides        of the formula (XIII)

-   -   in which    -   L, R⁶ and R⁷ have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) are very effective as pesticides, preferably as insecticides and/oracaricides and/or herbicides, are additionally frequently highlycompatible with plants, in particular with crop plants, and/or havefavourable toxicological and/or environmentally relevant properties.

Surprisingly, it has now also been found that certaincis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives,when used together with the crop plant compatibility-improving compounds(safeners/antidotes) described below, efficiently prevent damage to thecrop plants and can be used in a particularly advantageous manner asbroad-spectrum combination preparations for the selective control ofunwanted plants in crops of useful plants, such as, for example, incereals, but also in maize, soya beans and rice.

The invention also provides selective herbicidal compositions comprisingan effective amount of an active compound combination comprising, ascomponents,

-   (a′) at least one cis-alkoxyspirocyclic biphenyl-substituted    tetramic acid derivative of the formula (I), in which A, G, W, X, Y    and Z have the meaning given above    -   and-   (b′) at least one crop plant compatibility-improving compound from    the following group of compounds:    -   4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),        1-dichloroacetylhexa-hydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one        (dicyclonon, BAS-145138),        4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor),        1-methylhexyl 5-chloroquinoline-8-oxyacetate        (cloquintocet-mexyl—cf. also related compounds in EP-A-86750,        EP-A-94349, EP-A-191736, EP-A-492366),        3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),        α-(cyanomethoximino)phenylacetonitrile (cyometrinil),        2,4-dichlorophenoxyacetic acid (2,4-D),        4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),        1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron,        dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),        S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate        (dimepiperate),        2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)-acetamide        (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide(dichlormid),        4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl        1-(2,4-dichlorophenyl)-5-trichloro-methyl-1H-1,2,4-triazole-3-carboxylate        (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562        and EP-A-346620), phenylmethyl        2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),        4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone        oxime (fluxofenim),        3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine        (furilazole, MON-13900), ethyl        4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate        (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897),        1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate        (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA),        2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl        1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate        (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),        2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),        2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate        (MG-838), 1,8-naphthalic anhydride,        α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile        (oxabetrinil),        2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide        (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725),        3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),        4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric        acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate,        ethyl diphenylmethoxyacetate, methyl        1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl        1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl        1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,        ethyl        1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,        ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate        (cf. also related compounds in EP-A-269806 and EP-A-333131),        ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl        5-phenyl-2-isoxazoline-3-carboxylate, ethyl        5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf.        also related compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl        5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl        5-chloro-quinoline-8-oxyacetate, 1-allyloxyprop-2-yl        5-chloroquinoline-8-oxyacetate, methyl        5-chloroquinoxaline-8-oxyacetate, ethyl        5-chloroquinoline-8-oxyacetate, allyl        5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl        5-chloroquinoline-8-oxyacetate, diethyl        5-chloroquinoline-8-oxymalonate, diallyl        5-chloroquinoxaline-8-oxymalonate, diethyl        5-chloroquinoline-8-oxymalonate (cf. also related compounds in        EP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, cf.        EP-A-613618), 4-chlorophenoxyacetic acid,        3,3′-dimethyl-4-methoxybenzophenone,        1-bromo-4-chloromethylsulphonylbenzene,        1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also        known as        N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide),        1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,        1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)phenyl]-3-methylurea,        1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea,        N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide,        and/or one of the following compounds, defined by general        formulae        of the general formula (IIa)

or of the general formula (IIb)

or of the formula (IIc)

where

-   m represents a number 0, 1, 2, 3, 4 or 5,-   A¹ represents one of the divalent heterocyclic groupings shown below

-   n represents a number 0, 1, 2, 3, 4 or 5,-   A² represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl-    and/or C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2    carbon atoms,-   R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,-   R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy,    C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,-   R¹⁶ represents optionally fluorine-, chlorine- and/or    bromine-substituted C₁-C₄-alkyl,-   R¹⁷ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R¹⁸ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R¹⁷ and R¹⁸ also together represent C₃-C₆-alkanediyl or    C₂-C₅-oxaalkanediyl, each of which is optionally substituted by    C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or by two    substituents which, together with the C atom to which they are    attached, form a 5- or 6-membered carbocycle,-   R¹⁹ represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine-, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   R²⁰ represents hydrogen, in each case optionally hydroxyl-, cyano-,    halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl    or tri(C₁-C₄-alkyl)silyl,-   R²¹ represents hydrogen, cyano, halogen, or represents in each case    optionally fluorine-, chlorine- and/or bromine-substituted    C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,-   X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    and/or the following compounds, defined by general formulae    of the general formula (IId)

or of the general formula (IIe)

where

-   t represents a number 0, 1, 2, 3, 4 or 5,-   v represents a number 0, 1, 2, 3, 4 or 5,-   R²² represents hydrogen or C₁-C₄-alkyl,-   R²³ represents hydrogen or C₁-C₄-alkyl,-   R²⁴ represents hydrogen, in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, or in each case optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino,-   R²⁵ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,-   R²⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or    optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,    C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally C₁-C₄-alkyl-substituted    C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl,-   X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy, and-   X⁵ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   X preferably represents halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy or C₁-C₆-haloalkoxy,-   Z preferably represents the radicals

-   V¹, V² independently of one another preferably represent hydrogen,    halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl or    C₁-C₄-haloalkoxy,-   V³ preferably represents hydrogen, chlorine, bromine, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy,-   W and Y independently of one another preferably represent hydrogen,    halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or    C₁-C₆-haloalkoxy,-   A preferably represents C₁-C₆-alkyl,-   G preferably represents hydrogen (a) or represents one of the groups

in which

-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulphur and-   M represents oxygen or sulphur,-   R¹ represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,    C₁-C₈-alkylthio-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or    optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted    C₃-C₈-cycloalkyl in which optionally one or more (preferably not    more than two) not directly adjacent ring members are replaced by    oxygen and/or sulphur,    -   represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl,    -   represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or C₁-C₆-haloalkoxy-substituted        phenyl-C₁-C₆-alkyl,    -   represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or        6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,        pyrimidyl, furanyl or thienyl),    -   represents optionally halogen- or C₁-C₆-alkyl-substituted        phenoxy-C₁-C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl        (for example pyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl or        thiazolyloxy-C₁-C₆-alkyl),-   R² represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl,    poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,    -   represents optionally halogen-, C₁-C₆-alkyl- or        C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl, C₁-C₆-alkoxy-, C₁-C₆-haloalkyl- or        C₁-C₆-haloalkoxy-substituted phenyl or benzyl,-   R³ represents optionally halogen-substituted C₁-C₈-alkyl or    represents in each case optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- or    nitro-substituted phenyl or benzyl,-   R⁴ and R⁵ independently of one another represent in each case    optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,    C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each case    optionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,    C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-,    C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substituted phenyl, phenoxy or    phenylthio,-   R⁶ and R⁷ independently of one another represent hydrogen, represent    in each case optionally halogen-substituted C₁-C₈-alkyl,    C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,    C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,    C₁-C₈-haloalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,    optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- or    C₁-C₈-alkoxy-substituted benzyl or together represent an optionally    C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally    one methylene group is replaced by oxygen or sulphur.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   W particularly preferably represents hydrogen, methyl or chlorine,-   X particularly preferably represents fluorine, chlorine, bromine,    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy,-   Y particularly preferably represents hydrogen, C₁-C₄-alkyl,    fluorine, chlorine, bromine, methoxy or trifluoromethyl,-   Z particularly preferably represents the radicals

-   V¹, V² independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁-C₆-alkyl,    C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,-   V³ particularly preferably represents hydrogen, chlorine, bromine,    C₁-C₄-alkyl or C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,-   A particularly preferably represents C₁-C₄-alkyl,-   G particularly preferably represents hydrogen (a) or represents one    of the groups

-   -   in which

-   E represents a metal ion equivalent or an ammonium ion,

-   L represents oxygen or sulphur and

-   M represents oxygen or sulphur and

-   R¹ particularly preferably represents C₁-C₈-alkyl, C₂-C₁₈-alkenyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl each of which    is optionally mono- to trisubstituted by fluorine or chlorine, or    C₃-C₆-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, C₁-C₂-alkyl or C₁-C₂-alkoxy and in which    optionally one or two not directly adjacent ring members are    replaced by oxygen,    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,

-   R² particularly preferably represents C₁-C₈-alkyl, C₂-C₈-alkenyl or    C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine,    -   represents C₃-C₆-cycloalkyl which is optionally monosubstituted        by C₁-C₂-alkyl or C₁-C₂-alkoxy or    -   represents phenyl or benzyl, each of which is optionaly mono- or        disubstituted by fluorine, chlorine, bromine, cyano, nitro,        C₁-C₄-alkyl, C₁-C₃-alkoxy, trifluoromethyl or trifluoromethoxy,

-   R³ particularly preferably represents C₁-C₈-alkyl which is    optionally mono- to trisubstituted by fluorine or represents phenyl    which is optionally monosubstituted by fluorine, chlorine, bromine,    C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl, trifluoromethoxy, cyano    or nitro,

-   R⁴ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,    C₃-C₄-alkenylthio, C₃-C₆-cycloalkylthio or represents phenyl,    phenoxy or phenylthio, each of which is optionally monosubstituted    by fluorine, chlorine, bromine, nitro, cyano, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio, C₁-C₃-alkyl    or trifluoromethyl,

-   R⁵ particularly preferably represents C₁-C₆-alkoxy or    C₁-C₆-alkylthio,

-   R⁶ particularly preferably represents hydrogen, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, represents phenyl which is optionally    monosubstituted by fluorine, chlorine, bromine, trifluoromethyl,    C₁-C₄-alkyl or C₁-C₄-alkoxy, represents benzyl which is optionally    monosubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,    trifluoromethyl or C₁-C₄-alkoxy,

-   R⁷ particularly preferably represents C₁-C₆-alkyl, C₃-C₆-alkenyl or    C₁-C₆-alkoxy-C₁-C₄-alkyl,

-   R⁶ and R⁷ together particularly preferably represent a    C₄-C₅-alkylene radical which is optionally substituted by methyl or    ethyl and in which optionally one methylene group is replaced by    oxygen or sulphur.

In the radical definitions mentioned as being particularly preferred,halogen represents fluorine, chlorine and bromine, in particularlyfluorine and chlorine.

-   W very particularly preferably represents hydrogen or methyl,-   X very particularly preferably represents fluorine, chlorine,    methyl, ethyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy or    trifluoromethoxy,-   Y very particularly preferably represents hydrogen, methyl, fluorine    or chlorine,-   Z very particularly preferably represents the radicals

-   V¹, V² independently of one another very particularly preferably    represent hydrogen, fluorine, chlorine, methyl, ethyl, methoxy,    ethoxy, trifluoromethyl or trifluoromethoxy,-   V³ very particularly preferably represents hydrogen, chlorine,    methyl, methoxy, trifluoromethyl or trifluoromethoxy,-   A very particularly preferably represents methyl, ethyl, propyl or    butyl,-   G very particularly preferably represents hydrogen (a) or represents    one of the groups

-   -   in which

-   L represents oxygen or sulphur,

-   M represents oxygen or sulphur and

-   E represents an ammonium ion or a metal ion equivalent,

-   R¹ very particularly preferably represents C₁-C₆-alkyl,    C₂-C₁₇-alkenyl, C₁-C₂-alkoxy-C₁-alkyl, C₁-C₂-alkylthio-C₁-alkyl,    each of which is optionally monosubstituted by chlorine, or    represents cyclopropyl or cyclohexyl, each of which is optionally    monosubstituted by fluorine, chlorine, methyl or methoxy,    -   represents phenyl which is optionally monosubstituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy,        trifluoromethyl or trifluoromethoxy,

-   R² very particularly preferably represents C₁-C₈-alkyl,    C₂-C₆-alkenyl or C₁-C₄-alkoxy-C₂-C₃-alkyl, phenyl or benzyl, each of    which is optionally monosubstituted by fluorine.

-   W notably represents hydrogen or methyl,

-   X notably represents chlorine or methyl,

-   Y notably represents hydrogen or methyl,

-   Z notably represents the radicals

-   V¹, V² notably independently of one another represent hydrogen,    fluorine, chlorine, or methoxy,-   (Z represents in particular

-   A notably represents methyl or ethyl,-   G notably represents hydrogen (a) or represents one of the groups

-   -   in which

-   E represents a metal ion equivalent (Na⁺),

-   R¹ notably represents C₁-C₆-alkyl or cyclopropyl,

-   R² notably represents C₁-C₈-alkyl.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to precursors andintermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Noteworthiness in accordance with the invention is accorded to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being notable.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted unlessindicated otherwise, and in the case of multiple substitutions thesubstituents can be identical or different.

In addition to the compounds mentioned in the examples, the followingcompounds of the formula (I) may be specifically mentioned:

TABLE 1 where A = CH₃ W X Y F V¹ V² H Cl H 2 H H H Cl H 3 H H H Cl H 4 HH H Cl H 2 4-F H H Cl H 2 4-Cl H H Cl H 2 4-CH₃ H H Cl H 2 4-OCH₃ H H ClH 3 4-F H H Cl H 3 4-Cl H H Cl H 3 4-CH₃ H H Cl H 3 4-OCH₃ H H Cl H 43-Cl H H Cl H 4 3-CH₃ H H Cl H 4 3-OCH₃ H H Cl H 2 4-F 5-F H Cl H 2 4-F6-F H Cl H 2 4-Cl 5-F H Cl H 2 5-Cl 4-F H Cl H 3 4-F 5-F H CH₃ H 2 H H HCH₃ H 3 H H H CH₃ H 4 H H H CH₃ H 2 4-F H H CH₃ H 2 4-Cl H H CH₃ H 24-CH₃ H H CH₃ H 2 4-OCH₃ H H CH₃ H 3 4-F H H CH₃ H 3 4-Cl H H CH₃ H 34-CH₃ H H CH₃ H 3 4-OCH₃ H H CH₃ H 4 3-Cl H H CH₃ H 4 3-CH₃ H H CH₃ H 43-OCH₃ H H CH₃ H 2 4-F 5-F H CH₃ H 2 4-F 6-F H CH₃ H 2 4-Cl 5-F H CH₃ H2 5-Cl 4-F H CH₃ H 3 4-F 5-F CH₃ CH₃ H 2 H H CH₃ CH₃ H 3 H H CH₃ CH₃ H 4H H CH₃ CH₃ H 2 4-F H CH₃ CH₃ H 2 4-Cl H CH₃ CH₃ H 2 4-CH₃ H CH₃ CH₃ H 24-OCH₃ H CH₃ CH₃ H 3 4-F H CH₃ CH₃ H 3 4-Cl H CH₃ CH₃ H 3 4-CH₃ H CH₃CH₃ H 3 4-OCH₃ H CH₃ CH₃ H 4 3-Cl H CH₃ CH₃ H 4 3-CH₃ H CH₃ CH₃ H 43-OCH₃ H CH₃ CH₃ H 2 4-F 5-F CH₃ CH₃ H 2 4-F 6-F CH₃ CH₃ H 2 4-Cl 5-FCH₃ CH₃ H 2 5-Cl 4-F CH₃ CH₃ H 3 4-F 5-F H CH₃ CH₃ 2 H H H CH₃ CH₃ 3 H HH CH₃ CH₃ 4 H H H CH₃ CH₃ 2 4-F H H CH₃ CH₃ 2 4-Cl H H CH₃ CH₃ 2 4-CH₃ HH CH₃ CH₃ 2 4-OCH₃ H H CH₃ CH₃ 3 4-F H H CH₃ CH₃ 3 4-Cl H H CH₃ CH₃ 34-CH₃ H H CH₃ CH₃ 3 4-OCH₃ H H CH₃ CH₃ 4 3-Cl H H CH₃ CH₃ 4 3-CH₃ H HCH₃ CH₃ 4 3-OCH₃ H H CH₃ CH₃ 2 4-F 5-F H CH₃ CH₃ 2 4-F 6-F H CH₃ CH₃ 24-Cl 5-F H CH₃ CH₃ 2 5-Cl 4-F H CH₃ CH₃ 3 4-F 5-F CH₃ CH₃ CH₃ 2 H H CH₃CH₃ CH₃ 3 H H CH₃ CH₃ CH₃ 4 H H CH₃ CH₃ CH₃ 2 4-F H CH₃ CH₃ CH₃ 2 4-Cl HCH₃ CH₃ CH₃ 2 4-CH₃ H CH₃ CH₃ CH₃ 2 4-OCH₃ H CH₃ CH₃ CH₃ 3 4-F H CH₃ CH₃CH₃ 3 4-Cl H CH₃ CH₃ CH₃ 3 4-CH₃ H CH₃ CH₃ CH₃ 3 4-OCH₃ H CH₃ CH₃ CH₃ 43-Cl H CH₃ CH₃ CH₃ 4 3-CH₃ H CH₃ CH₃ CH₃ 4 3-OCH₃ H CH₃ CH₃ CH₃ 2 4-F5-F CH₃ CH₃ CH₃ 2 4-F 6-F CH₃ CH₃ CH₃ 2 4-Cl 5-F CH₃ CH₃ CH₃ 2 5-Cl 4-FCH₃ CH₃ CH₃ 3 4-F 5-FTable 2: W, X, Y, F, V¹ and V² as stated in Table 1

-   -   where A=C₂H₅        Table 3: W, X, Y, F, V¹ and V² as stated in Table 1    -   where A=C₃H₇        Table 4: W, X, Y, F, V¹ and V² as stated in Table 1    -   where A=C₄H₉

Preferred meanings of the groups listed above in connection with thecrop plant compatibility-improving compounds (“herbicide safeners”) ofthe formulae (IIa), (IIb), (IIc), (IId) and (IIe) are defined below.

-   m preferably represents the numbers 0, 1, 2, 3 or 4.-   A¹ preferably represents one of the divalent heterocyclic groupings    shown below

-   n preferably represents the numbers 0, 1, 2, 3 or 4.-   A² preferably represents in each case optionally methyl-, ethyl-,    methoxycarbonyl-, ethoxycarbonyl- or alkoxy carbonyl-substituted    methylene or ethylene.-   R¹⁴ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino.-   R¹⁵ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy,    allyloxy, 1-allyloxymethylethoxy, methylthio, ethylthio, n- or    i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n-    or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or    diethylamino.-   R¹⁶ preferably represents in each case optionally fluorine-,    chlorine- and/or bromine-substituted methyl, ethyl, n- or i-propyl.-   R¹⁷ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl.-   R¹⁸ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, i-, s- or t-butyl-substituted phenyl, or together    with R¹⁷ represents one of the radicals —CH₂—O—CH₂—CH₂— and    —CH₂—CH₂—O—CH₂—CH₂— which are optionally substituted by methyl,    ethyl, furyl, phenyl, a fused benzene ring or by two substituents    which, together with the C atom to which they are attached, form a    5- or 6-membered carbocycle.-   R¹⁹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl,    cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   R²⁰ preferably represents hydrogen, optionally hydroxyl-, cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.-   R²¹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-    or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or    phenyl.-   X¹ preferably represents nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chloro-difluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X² preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X³ preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   t preferably represents the numbers 0, 1, 2, 3 or 4.-   v preferably represents the numbers 0, 1, 2, 3 or 4.-   R²² preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²⁴ preferably represents hydrogen, in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,    ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio,    ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,    methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or    t-butylamino, dimethylamino or diethylamino, or in each case    optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-,    n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,    cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,    cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio,    cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino    or cyclohexylamino.-   R²⁵ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, or in    each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl.-   R²⁶ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, in each    case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally methyl- or    ethyl-substituted butane-1,4-diyl(trimethylene), pentane-1,5-diyl,    1-oxabutane-1,4-diyl or 3-oxapentane-1,5-diyl.-   X⁴ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.-   X⁵ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulphamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,    methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or    trifluoromethoxy.

Examples of the compounds of the formula (Ha) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIa) (IIa)

Example (Positions) No. (X¹)_(m) A¹ R¹⁴ IIa-1 (2) Cl, (4) Cl

OCH₃ IIa-2 (2) Cl, (4) Cl

OCH₃ IIa-3 (2) Cl, (4) Cl

OC₂H₅ IIa-4 (2) Cl, (4) Cl

OC₂H₄ IIa-5 (2) Cl

OCH₃ IIa-6 (2) Cl, (4) Cl

OCH₃ IIa-7 (2) F

OCH₃ IIa-8 (2) F

OCH₃ IIa-9 (2) Cl, (4) Cl

OC₂H₅ IIa-10 (2) Cl, (4) CF₃

OCH₃ IIa-11 (2) Cl

OCH₃ IIa-12 —

OC₂H₅ IIa-13 (2) Cl, (4) Cl

OC₂H₅ IIa-14 (2) Cl, (4) Cl

OC₂H₅ IIa-15 (2) Cl, (4) Cl

OC₂H₅ IIa-16 (2) Cl, (4) Cl

OC₂H₅ IIa-17 (2) Cl, (4) Cl

OC₂H₅ IIa-18 —

OH

Examples of the compounds of the formula (IIb) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIb) Ex- (Posi- ampletion) (Position) No. X² X³ A² R¹⁵ IIb-1 (5) — CH₂ OH Cl IIb-2 (5) — CH₂OCH₃ Cl IIb-3 (5) — CH₂ OC₂H₅ Cl IIb-4 (5) — CH₂ OC₃H₇-n Cl IIb-5 (5) —CH₂ OC₃H₇-i Cl IIb-6 (5) — CH₂ OC₄H₉-n Cl IIb-7 (5) — CH₂OCH(CH₃)C₅H₁₁-n Cl IIb-8 (5) (2) CH₂ OH Cl F IIb-9 (5) (2) CH₂ OH Cl ClIIb-10 (5) — CH₂ OCH₂CH═CH₂ Cl IIb-11 (5) — CH₂ OC₄H₉-i Cl IIb-12 (5) Cl— CH₂

IIb-13 (5) Cl —

OCH₂CH═CH₂ IIb-14 (5) Cl —

OC₂H₅ IIb-15 (5) Cl —

OCH₃

Examples of the compounds of the formula (IIc) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIc) Example No. R¹⁶N(R¹⁷,R¹⁸⁾ IIc-1 CHCl₂ N(CH₂CH═CH₂)₂ IIc-2 CHCl₂

IIc-3 CHCl₂

IIc-4 CHCl₂

IIc-5 CHCl₂

IIc-6 CHCl₂

IIc-7 CHCl₂

Examples of the compounds of the formula (IId) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IId) Example (Positions)(Positions) No. R²² R²³ R²⁴ (X⁴)_(t) (X⁵)_(v) IId-1 H H CH₃ (2) OCH₃ —IId-2 H H C₂H₅ (2) OCH₃ — IId-3 H H C₃H₇-n (2) OCH₃ — IId-4 H H C₃H₂-i(2) OCH₃ — IId-5 H H

(2) OCH₃ — IId-6 H H CH₃ (2) OCH₃ — (5) CH₃ IId-7 H H C₂H₅ (2) OCH₃ —(5) CH₃ IId-8 H H C₃H₇-n (2) OCH₃ — (5) CH₃ IId-9 H H C₃H₇-i (2) OCH₃ —(5) CH₃ IId-10 H H

(2) OCH₃ (5) CH₃ — IId-11 H H OCH₃ (2) OCH₃ — (5) CH₃ IId-12 H H OC₂H₅(2) OCH₃ — (5) CH₃ IId-13 H H OC₃H₇-i (2) OCH₃ — (5) CH₃ IId-14 H H SCH₃(2) OCH₃ — (5) CH₃ IId-15 H H SC₂H₅ (2) OCH₃ — (5) CH₃ IId-16 H HSC₃H₇-i (2) OCH₃ — (5) CH₃ IId-17 H H NHCH₃ (2) OCH₃ — (5) CH₃ IId-18 HH NHC₂H₅ (2) OCH₃ — (5) CH₃ IId-19 H H NHC₃H₇-i (2) OCH₃ — (5) CH₃IId-20 H H

(2) OCH₃ (5) CH₃ — IId-21 H H NHCH₃ (2) OCH₃ — IId-22 H H NHC₃H₇-i (2)OCH₃ — IId-23 H H N(CH₃)₂ (2) OCH₃ — IId-24 H H N(CH₃)₂ (3) CH₃ — (4)CH₃ IId-25 H H CH₂—O—CH₃ (2) OCH₃ —

Examples of the compounds of the formula (Ile) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIe) Example (Positions)(Positions) No. R²² R²⁵ R²⁶ (X⁴)_(t) (X⁵)_(v) IIe-1 H H CH₃ (2) OCH₃ —IIe-2 H H C₂H₅ (2) OCH₃ — IIe-3 H H C₃H₇-n (2) OCH₃ — IIe-4 H H C₃H₇-i(2) OCH₃ — IIe-5 H H

(2) OCH₃ — IIe-6 H CH₃ CH₃ (2) OCH₃ — IIe-7 H H CH₃ (2) OCH₃ — (5) CH₃IIe-8 H H C₂H₅ (2) OCH₃ — (5) CH₃ IIe-9 H H C₃H₇-n (2) OCH₃ — (5) CH₃IIe-10 H H C₃H₇-i (2) OCH₃ — (5) CH₃ IIe-11 H H

(2) OCH₃ (5) CH₃ — IIe-12 H CH₃ CH₃ (2) OCH₃ — (5) CH₃

Most preferred as crop plant compatibility-improving compound [component(b′)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperateand the compounds IIe-5 and IIe-11, and particular emphasis is given tocloquintocet-mexyl and mefenpyr-diethyl, but also to isoxachifen-ethyl.

The compounds of the general formula (IIa) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. WO-A-91/07874, WO-A-95/07897).

The compounds of the general formula (IIb) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. EP-A-191736).

The compounds of the general formula (IIc) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-2218097, DE-A-2350547).

The compounds of the general formula (IId) to be used as safenersaccording to the invention are known and/or can be prepared by processesknown per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680).

The compounds of the general formula (IIe) to be used as safenersaccording to the invention are known and can be prepared by processesknown per se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).

Examples of the selective herbicidal combinations according to theinvention comprising in each case one active compound of the formula (I)and one of the safeners defined above are listed in the table below.

TABLE Examples of combinations according to the invention Activecompounds of the formula (I) Safener I-a cloquintocet-mexyl I-afenchlorazole-ethyl I-a isoxadifen-ethyl I-a mefenpyr-diethyl I-afurilazole I-a fenclorim I-a cumyluron I-a daimuron/dymron I-adimepiperate I-a IIe-11 I-a IIe-5 I-b cloquintocet-mexyl I-bfenchlorazole-ethyl I-b isoxadifen-ethyl I-b mefenpyr-diethyl I-bfurilazole I-b fenclorim I-b cumyluron I-b daimuron/dymron I-bdimepiperate I-b IIe-11 I-b IIe-5 I-c cloquintocet-mexyl I-cfenchlorazole-ethyl I-c isoxadifen-ethyl I-c mefenpyr-diethyl I-cfurilazole I-c fenclorim I-c cumyluron I-c daimuron/dymron I-cdimepiperate I-c IIe-5 I-c IIe-11 I-d cloquintocet-mexyl I-dfenchlorazole-ethyl I-d isoxadifen-ethyl I-d mefenpyr-diethyl I-dfurilazole I-d fenclorim I-d cumyluron I-d daimuron/dymron I-ddimepiperate I-d IIe-11 I-d IIe-5 I-e cloquintocet-mexyl I-efenchlorazole-ethyl I-e isoxadifen-ethyl I-e mefenpyr-diethyl I-efurilazole I-e fenclorim I-e cumyluron I-e daimuron/dymron I-edimepiperate I-e IIe-5 I-e IIe-11 I-f cloquintocet-mexyl I-ffenchlorazole-ethyl I-f isoxadifen-ethyl I-f mefenpyr-diethyl I-ffurilazole I-f fenclorim I-f cumyluron I-f daimuron/dymron I-fdimepiperate I-f IIe-5 I-f IIe-11 I-g cloquintocet-mexyl I-gfenchlorazole-ethyl I-g isoxadifen-ethyl I-g mefenpyr-diethyl I-gfurilazole I-g fenclorim I-g cumyluron I-g daimuron/dymron I-gdimepiperate I-g IIe-5 I-g IIe-11

Surprisingly, it has now been found that the active compoundcombinations, defined above, of cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives of the general formula(I) and safeners (antidotes) from group (b′) listed above, while beingvery well tolerated by useful plants, have a particularly highherbicidal activity and can be used in various crops, in particular incereals (especially wheat), but also in soya beans, potatoes, maize andrice, for the selective control of weeds.

Here, it has to be considered surprising that, from a large number ofknown safeners or antidotes capable of antagonizing the harmful effectof a herbicide on crop plants, those suitable are in particular thecompounds of group (b′) listed above which eliminate the harmful effectof cis-alkoxy-spirocyclic biphenyl-substituted tetramic acid derivativeson the crop plants virtually completely without having a major adverseeffect on the herbicidal activity against the weeds.

Emphasis may be given here to the particularly advantageous effect ofthe particularly and most preferred combination partners from group(b′), in particular with respect to sparing cereal plants, such as, forexample, wheat, barley and rye, but also maize and rice, as crop plants.

In the literature it has already been described how the action ofvarious active compounds can be boosted by addition of ammonium salts.The salts in question, however, are detersive salts (for example WO95/017817) or salts which have relatively long alkyl substituents and/oraryl substituents and which have a permeabilizing action or whichincrease the active compound's solubility (for example EP-A 0 453 086,EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No.5,462,912, U.S. Pat. No. 5,538,937, U.S. Ser. No. 03/0224,939, U.S. Ser.No. 05/0009,880, U.S. Ser. No. 05/0096,386). Moreover, the prior artdescribes the action only for particular active compounds and/orparticular applications of the corresponding compositions. In othercases, in turn, the salts in question are those of sulphonic acids,where the acids themselves have a paralytic action on insects (U.S. Pat.No. 2,842,476). A boost to action by ammonium sulphate, for example, isdescribed by way of example for the herbicides glyphosate,phosphinothricin and certain cyclic ketoenols (U.S. Pat. No. 6,645,914,EP-A2 0 036 106, WO 07/068427). A corresponding action in the case ofinsecticides is described for certain cyclic ketoenols in WO 07/068428.

The use of ammonium sulphate as a formulating assistant has also beendescribed for certain active compounds and applications (WO 92/16108),but its purpose therein is to stabilize the formulation, not to boostthe action.

It has now been found, surprisingly, that the action of insecticidesand/or acaricides and/or herbicides from the class of thecis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives ofthe formula (I) can be boosted significantly through the addition ofammonium salts or phosphonium salts to the application solution orthrough the incorporation of these salts into a formulation comprisingcis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives ofthe formula (I). The present invention therefore provides for the use ofammonium salts or phosphonium salts for boosting the action of cropprotection compositions which comprise as their active compoundinsecticidal and/or acaricidal cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives of the formula (I). Theinvention likewise provides compositions which comprise herbicidaland/or acaricidal and/or insecticidal cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives of the formula (I) andaction-boosting ammonium salts or phosphonium salts, including not onlyformulated active compounds but also ready-to-use compositions (sprayliquors). The invention further provides, finally, for the use of thesecompositions for controlling insect pests and/or spider mites and/orunwanted plant growth.

The compounds of the formula (I) possess a broad insecticidal and/oracaricidal and/or herbicidal activity, but in specific cases theactivity and/or plant tolerance leaves something to be desired. However,some or all of these properties can be improved by adding ammonium saltsor phosphonium salts.

The active compounds can be used in the compositions according to theinvention in a broad concentration range. The concentration of theactive compounds in the formulation is typically 0.1%-50% by weight.

The formula (III′) provides a definition of the ammonium salts andphosphonium salts which, according to the invention, boost the activityof crop protection compositions comprising an active compound from theclass of the cis-alkoxyspirocyclic biphenyl-substituted tetramic acidderivatives of the formula (I)

in which

-   D represents nitrogen or phosphorus,-   D preferably represents nitrogen,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another represent    hydrogen or in each case optionally substituted C₁-C₈-alkyl or mono-    or polyunsaturated, optionally substituted C₁-C₈-alkylene, the    substituents being selectable from halogen, nitro and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another preferably    represent hydrogen or in each case optionally substituted    C₁-C₁-alkyl, the substituents being selectable from halogen, nitro    and cyano,-   R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another particularly    preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl or tert-butyl,-   R²⁶, R²⁷, R²⁸ and R²⁹ very particularly preferably represent    hydrogen,-   n represents 1, 2, 3 or 4,-   n preferably represents 1 or 2,-   R³⁰ represents an organic or inorganic anion,-   R³⁰ preferably represents hydrogencarbonate, tetraborate, fluoride,    bromide, iodide, chloride, monohydrogenphosphate,    dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate,    thiosulphate, thiocyanate, formate, lactate, acetate, propionate,    butyrate, pentanoate or oxalate,-   R³⁰ particularly preferably represents lactate, sulphate, nitrate,    thiosulphate, thiocyanate, oxalate or formate.-   R³⁰ very particularly preferably represents sulphate.

Inventively emphasized combinations of active compound, salt andpenetrant are listed in the table below. “Penetrant as per test” meanshere that any compound that acts as a penetrant in the cuticlepenetration test (Baur et al., 1997, Pesticide Science 51, 131-152) issuitable.

The ammonium salts and phosphonium salts of the formula (III′) can beused in a broad concentration range to boost the activity of cropprotection compositions comprising cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives of the formula (I). Ingeneral the ammonium salts or phosphonium salts are used in theready-to-use crop protection composition in a concentration of 0.5 to 80mmol/l, preferably 0.75 to 37.5 mmol/l, more preferably 1.5 to 25mmol/l. In the case of a formulated product the ammonium salt and/orphosphonium salt concentration in the formulation is chosen such that itis within these stated general, preferred or particularly preferredranges after the formulation has been diluted to the desired activecompound concentration. The concentration of the salt in the formulationis typically 1%-50% by weight.

In one preferred embodiment of the invention the activity is boosted byadding to the crop protection compositions not only an ammonium saltand/or phosphonium salt but also, additionally, a penetrant. It isconsidered entirely surprising that even in these cases an even greaterboost to activity is observed. The present invention therefore likewiseprovides for the use of a combination of penetrant and ammonium saltsand/or phosphonium salts to boost the activity of crop protectioncompositions which comprise insecticidal cis-alkoxyspirocyclicbiphenyl-substituted tetramic acid derivatives of the formula (I) asactive compound. The invention likewise provides compositions whichcomprise herbicidal and/or acaricidal and/or insecticidalcis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives ofthe formula (I), penetrants and ammonium salts and/or phosphonium salts,including specifically not only formulated active compounds but alsoready-to-use compositions (spray liquors). The invention additionallyprovides, finally, for the use of these compositions for controllingharmful insects and/or spider mites.

In the present context, suitable penetrants are all those substanceswhich are usually employed to improve penetration of agrochemicallyactive compounds into plants. In this context, penetrants are defined inthat they penetrate from the aqueous spray liquor and/or the spraycoating into the cuticles of the plant, thus increasing the mobility ofactive compounds in the cuticles. The method described in the literature(Baur et al., 1997, Pesticide Science 51, 131-152) can be used fordetermining this property.

Examples of suitable penetrants include alkanol alkoxylates. Penetrantsof the invention are alkanol alkoxylates of the formula (IV′)R—O-(-AO)_(v)—R′  (IV′)in which

-   -   R is linear or branched alkyl having 4 to 20 carbon atoms,    -   R′ is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,        isobutyl, tert-butyl, n-pentyl or n-hexyl,    -   AO is an ethylene oxide radical, a propylene oxide radical, a        butylene oxide radical or is mixtures of ethylene oxide and        propylene oxide radicals or butylene oxide radicals, and    -   v is a number from 2 to 30.

One preferred group of penetrants are alkanol alkoxylates of the formulaR—O-(-EO—)_(n)—R′  (IV′-a)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—O—CH₂—O—, and    -   n is a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O-(-EO—)_(p)—(—PO—)_(q)—R′  (IV′-b)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   p is a number from 1 to 10, and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—PO—)_(r)-(EO—)_(s)—R′  (IV′-c)in which

-   -   R is as defined above,    -   R′ is as defined above,    -   EO is —CH₂—CH₂—O—,    -   PO is

-   -   r is a number from 1 to 10, and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O-(-EO—)_(p)—(—BO—)_(q)—R′  (IV′-d)in which

-   -   R and R′ are as defined above,    -   EO is CH₂—CH₂—O—,    -   BO is

-   -   p is a number from 1 to 10 and    -   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—BO—)_(r)-(-EO—)_(s)—R′  (IV′-e)in which

-   -   R and R′ are as defined above,    -   BO is

-   -   EO is CH₂—CH₂—O—,    -   r is a number from 1 to 10 and    -   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaCH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—R′  (IV′-f)in which

-   -   R′ is as defined above,    -   t is a number from 8 to 13,    -   u is a number from 6 to 17.

In the formulae indicated above,

-   R is preferably butyl, isobutyl, n-pentyl, isopentyl, neopentyl,    n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl,    decyl, n-dodecyl, isododecyl, lauryl, myristyl, isotridecyl,    trimethylnonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (IV′-c) mentionmay be made of 2-ethylhexyl alkoxylate of the formula

in which

-   -   EO is —CH₂—CH₂—O—,    -   PO is

and the numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (IV′-d) mentionmay be made of the formulaCH₃—(CH₂)₁₀—O-(-EO—)₆—(—BO—)₂—CH₃  (IV′-d-1)in which

-   -   EO is CH₂—CH₂—O—,    -   BO is

and the numbers 10, 6 and 2 represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) arecompounds of this formula in which

-   -   t is a number from 9 to 12 and    -   u is a number from 7 to 9.

Mention may be made with very particular preference of alkanolalkoxylate of the formula (IV′-f-1)CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—H  (IV′-f-1)in which

-   -   t stands for the average value 10.5 and    -   u stands for the average value 8.4.

A general definition of the alkanol alkoxylates is given by the formulaeabove. These substances are mixtures of compounds of the stated typewith different chain lengths. The indices therefore have average valueswhich may also deviate from whole numbers.

The alkanol alkoxylates of the formulae stated are known and in somecases are available commercially or can be prepared by known methods(cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Suitable penetrants also include, for example, substances which promotethe availability of the compounds of the formula (I) in the spraycoating. These include, for example, mineral or vegetable oils. Suitableoils are all mineral or vegetable oils—modified or otherwise—which cantypically be used in agrochemical compositions. Mention may be made byway of example of sunflower oil, rapeseed oil, olive oil, castor oil,colza oil, maize seed oil, cotton seed oil and soya bean oil, or theesters of said oils. Preference is given to rapeseed oil, sunflower oiland their methyl or ethyl esters.

The concentration of penetrant in the compositions of the invention canbe varied within a wide range. In the case of a formulated cropprotection composition it is in general 1% to 95%, preferably 1% to 55%,more preferably 15%-40% by weight. In the ready-to-use compositions(spray liquors) the concentrations are generally between 0.1 and 10 g/l,preferably between 0.5 and 5 g/l.

Crop protection compositions of the invention may also comprise furthercomponents, examples being surfactants and/or dispersing assistants oremulsifiers.

Suitable nonionic surfactants and/or dispersing assistants include allsubstances of this type that can typically be used in agrochemicalcompositions. Preferably mention may be made of polyethyleneoxide-polypropylene oxide block copolymers, polyethylene glycol ethersof linear alcohols, reaction products of fatty acids with ethylene oxideand/or propylene oxide, and also polyvinyl alcohol,polyvinylpyrrolidone, copolymers of polyvinyl alcohol andpolyvinylpyrrolidone, and copolymers of (meth)acrylic acid and(meth)acrylic esters, and additionally alkyl ethoxylates and alkylarylethoxylates, which optionally may be phosphated and optionally may beneutralized with bases, mention being made, by way of example, ofsorbitol ethoxylates, and, as well, polyoxyalkylenamine derivatives.

Suitable anionic surfactants include all substances of this type thatcan typically be used in agrochemical compositions. Preference is givento alkali metal salts and alkaline earth metal salts of alkylsulphonicacids or alkylarylsulphonic acids.

A further preferred group of anionic surfactants and/or dispersingassistants are the following salts that are of low solubility in plantoil: salts of polystyrenesulphonic acids, salts of polyvinylsulphonicacids, salts of naphthalenesulphonic acid-formaldehyde condensationproducts, salts of condensation products of naphthalenesulphonic acid,phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.

Suitable additives which may be included in the formulations of theinvention are emulsifiers, foam inhibitors, preservatives, antioxidants,colorants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products ofalkylphenols with ethylene oxide and/or propylene oxide, ethoxylatedarylalkylphenols, and also ethoxylated and propoxylatedarylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylatesand/or arylalkyl ethoxypropoxylates, mention being made by way ofexample of sorbitan derivatives, such as polyethylene oxide-sorbitanfatty acid esters, and sorbitan fatty acid esters.

Using, for example, according to process (A) ethylcis-N-[(2,6-dimethyl-3-(4-fluorophenyl)acetyl]-1-amino-4-methoxycyclohexane-1-carboxylateas starting material, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, according to process (B),cis-8-methoxy-3-(3-bromo-2,6-dimethylphenyl)-1-azaspiro-[4,5]decane-2,4-dioneand 4-fluorophenylboronic acid as starting materials, the course of thereaction can be represented by the scheme below:

Using, for example, according to process (Cα)cis-8-methoxy-3-[6-methyl-3-(4-fluorophenyl)-1-phenyl]-1-azaspiro[4,5]decane-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (C) (variant β)cis-8-methoxy-3-[6-methyl-3-(4-fluoro-phenyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (D)cis-8-methoxy-3-[2-chlor-5-(3,4-difluorophenyl)-phenyl]-1-azaspiro[4,5]decane-2,4-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the reactionscheme below:

Using, for example, according to process (E), variant (α),cis-8-methoxy-3-[2-chloro-5-(4-fluoro-phenyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using, for example, according to process (E), variant (β),cis-8-methoxy-3-[2,6-dimethyl-3-(4-fluorophenyl)phenyl]-1-azaspiro[4,5]decane-2,4-dione,carbon disulphide and methyl iodide as starting materials, the course ofthe reaction can be represented as follows:

Using, for example, according to process (F)cis-8-methoxy-3-[2-chloro-5-(4-fluorophenyl)-phenyl]-1-azaspiro[4,5]decane-2,4-dioneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the reaction scheme below:

Using, for example, according to process (G)cis-8-methoxy-3-[6-methyl-3-(3,4-difluorophenyl)-phenyl]-1-azaspiro[4,5]decane-2,4-dioneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by the reactionscheme below:

Using, for example, according to process (H)cis-8-methoxy-3-[2,6-dimethyl-3-(4-fluorophenyl)-phenyl]-1-azaspiro[4,5]decane-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (I) variant (α)cis-8-methoxy-3-[6-methyl-3-(3,4-difluorophenyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the reaction scheme below:

Using, for example, according to process (I) variant (β)cis-8-methoxy-3-[2-chloro-5-(4-fluoro-phenyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the scheme below:

The compounds, required as starting materials for the process (a)according to the invention, of the formula (II)

in whichA, W, X, Y, Z and R⁸ have the meanings given above,are novel.

The acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XIV)

in which

-   A and R⁸ have the meanings given above,-   are acylated with substituted phenyl acetic acid derivatives of the    formula (XV)

in which

-   W, X, Y and Z have the meanings given above and-   U represents a leaving group introduced by reagents for activating    carboxylic acids, such as carbonyldiimidazole, carbonyldiimides    (such as, for example, dicyclohexylcarbodiimide), phosphorylating    reagents (such as, for example, POCl₃, BOP-Cl), halogenating agents,    such as, for example, thionyl chloride, oxalyl chloride, phosgene or    chloroformic esters,-   (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6,    341-5, 1968)-   or when acylamino acids of the formula (XVI)

in which

-   A, W, X, Y and Z have the meanings given above,-   are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XVI)

in whichA, W, X, Y and Z have the meanings given above,are novel.

The compounds of the formula (XVI) are obtained when amino acids of theformula (XVII)

in whichA has the meaning given above,are acylated with substituted phenylacetic acid derivatives of theformula (XV)

in whichW, X, Y and Z have the meanings given above andU has the meaning given above,for example according to Schotten-Baumann (Organikum, VEB DeutscherVerlag der Wissen-schaften, Berlin 1977, p. 505).

The compounds of the formula (XV) are novel. They can be obtained bymethods known in principle (see, for example, H. Henecka, Houben-Weyl,Methoden der Organischen Chemie [Methods of organic chemistry], Vol. 8,pp. 467-469 (1952) or according to the patent applications cited at theoutset).

The compounds of the formula (XV) are obtained, for example, whensubstituted phenylacetic acids of the formula (XVIII)

in whichW, X, Y and Z have the meaning given aboveare reacted with halogenating reagents (for example thionyl chloride,thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride,phosphorus tribromide or phosphorus pentachloride) or phosphorylatingreagents (for example POCl₃, BOP-Cl) if appropriate in the presence of adiluent (for example optionally chlorinated aliphatic or aromatichydrocarbons, such as toluene or methylene chloride) at temperatures offrom −20° C. to 150° C., preferably from −10° C. to 100° C.

Some of the compounds of the formulae (XIV) and (XVII) are known from WO02/002532, and/or they can be prepared by known processes.

Some of the compounds of the formula (XVIII) are known from WO2005/016873 or can be prepared by the processes described therein.

For example, the compounds of the formula (XVIII),

in whichW, X, Y and Z have the meanings given aboveare obtainedα) when compounds of the formula (XVIII-a)

in whichX and Y have the meaning given above,Z′ represents chlorine, bromine or iodine, preferably bromine,are reacted with boronic acids or boronic acid derivatives of theformula (III)

in whichZ and R⁹ have the meaning given above,in the presence of a solvent, a base and a catalyst (preferably apalladium salt or palladium complex, such as, for example,palladiumtetrakis(triphenylphosphine)) orβ) when phenylacetic esters of the formula (XIX)

in whichW, X, Y, Z and R⁸ have the meaning given above,are hydrolysed in the presence of acids or bases, in the presence of asolvent, under generally known standard conditions orγ) when phenylacetic acids of the formula (XVIII-b)

in whichW, X and Z have the meaning given aboveare reacted with halogen compounds of the formula (XX),Z-Hal  (XX)in whichZ has the meaning given above andHal represents chlorine, bromine or iodine, preferably bromine oriodine,in the presence of a solvent, a base and a catalyst (preferably apalladium salt or one of the palladium complexes mentioned above).

Some of the compounds of the formulae (III) and (XX) are known, some arecommercially available, or they can be prepared by processes known inprinciple. Some of the phenylacetic acids of the formula (XVIII-a) areknown from WO 97/01 535, WO 97/36 868 and WO 98/05 638, or they can beprepared by the processes described therein.

Some of the compounds of the formula (XIX) are known from WO2005/016873, or they can be prepared by the processes described therein.

The compounds of the formula (XVIII-b) are known from WO 05/016873.

The compounds of the formula (XIX)

in whichW, X, Y, Z and R⁸ have the meaning given above,are obtained, for example,when phenylacetic esters of the formula (XIX-a)

in whichR⁸, W, X, Y and Z′ have the meaning given above,are reacted with boronic acids or boronic acid derivatives of theformula (III)

in whichZ and R⁹ have the meaning given above,in the presence of a solvent, a base and a catalyst (preferably apalladium salt or one of the palladium complexes mentioned above).

Some of the phenyl acetic esters of the formula (XIX-a) are known fromthe applications WO 97/01535, WO 97/36868 and WO 98/0563, or they can beprepared by the processes described therein.

Some of the compounds, required as starting materials in the aboveprocess (C), of the formulae (I-a′) to (I-g′) in which A, W, X and Yhave the meaning given above and Z′ represents chlorine, bromine oriodine, preferably bromine, are known (WO 96/35 664, WO 97/02 243 and WO98/05 638), or they can be prepared according to the processes describedtherein.

Some of the boronic acids and boronic acid derivatives of the formula(III)

in whichZ and R⁹ have the meaning given aboveare commercially available, or they can be prepared in a simple mannerby generally known processes.

The acid halides of the formula (IV), carboxylic anhydrides of theformula (V), chloroformic esters or chloroformic thioesters of theformula (VI), chloromonothioformic esters or chlorodithioformic estersof the formula (VII), sulphonyl chlorides of the formula (VIII),phosphorus compounds of the formula (IX) and metal hydroxides, metalalkoxides or amines of the formulae (X) and (XI), respectively, andisocyanates of the formula (XII) and carbamoyl chlorides of the formula(XIII) furthermore required as starting materials for carrying out theprocesses (D), (E), (F), (G), (H), (I) and (J) according to theinvention are generally known compounds of organic or inorganicchemistry.

The process (A) is characterized in that compounds of the formula (II),in which A, W, X, Y, Z and R⁸ have the meanings given above aresubjected to an intramolecular condensation in the presence of a base.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, isopropanol,butanol, isobutanol and tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which may also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris(methoxyethoxyethyl)amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Furthermore, it is possibleto employ alkali metals and alkaline earth metal amides and hydrides,such as sodium amide, sodium hydride and calcium hydride, andadditionally also alkali metal alkoxides, such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

When carrying out the process (A) according to the invention, thereaction temperatures may be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in about doubly equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

Suitable catalysts for carrying out the process (B) according to theinvention are palladium(0) complexes. Preference is given, for example,to tetrakis(triphenylphosphine)palladium. If appropriate, it is alsopossible to use palladium(II) salts, for example PdCl₂, Pd(NO₃)₂.

Suitable acid acceptors for carrying out the process (B) according tothe invention are inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydroxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydroxide, potassiumhydroxide, barium hydroxide or ammonium hydroxide, sodium acetate,potassium acetate, calcium acetate or ammonium acetate, sodiumcarbonate, potassium carbonate or ammonium carbonate, sodium bicarbonateor potassium bicarbonate, alkali metal fluorides, such as, for example,caesium fluoride, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diaza-bicycloundecene (DBU).

Suitable diluents for carrying out the process (B) according to theinvention are water, organic solvents and any mixtures thereof. Exampleswhich may be mentioned are: aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;halogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride,dichloroethane, trichloroethane or tetrachloroethylene; ethers, such asdiethyl ether, diisopropyl ether, methyl-t-butyl ether, methyl-t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole;alcohols, such as methanol, ethanol, n- or i-propanol, n-, iso-, sec- ortert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether; water.

In the process (B) according to the invention, the reaction temperaturecan be varied within a relatively wide range. In general, the process iscarried out at temperatures between 0° C. and +140° C., preferablybetween 50° C. and +100° C.

When carrying out the process (B) according to the invention, theboronic acid(s) derivatives of the formula (III) in which Z has themeaning given above and the compounds of the formulae (I-a′) to (I-g′),in which A, W, X, Y and Z′ have the meaning given above are employed ina molar ratio of from 1:1 to 3:1, preferably from 1:1 to 2:1. Thecatalyst is generally added in amounts of from 0.005 to 0.5 mol,preferably from 0.01 mol to 0.1 mol, per mole of the compounds of theformulae (I-a′) to (I-g′). The base is generally employed in excess.

The process (C-α) is characterized in that compounds of the formula(I-a) are each reacted with carbonyl halides of the formula (IV), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (C-α) according to theinvention are all solvents inert towards the acid halides. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. If the acid halide is sufficiently stable tohydrolysis, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction according to the process (C-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

The reaction temperatures in the process (C-α) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C-α) according to the invention, thestarting materials of the formula (I-a) and the carbonyl halide of theformula (IV) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of the carbonyl halide. Work-up is carried out bycustomary methods.

The process (C-β) is characterized in that compounds of the formula(I-a) are each reacted with carboxylic anhydrides of the formula (V), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (C-β) according to theinvention are, preferably, the diluents which are also preferred whenusing acid halides. Besides, excess carboxylic anhydride maysimultaneously act as diluent.

Suitable acid binders, which are added, if appropriate, for process(C-β) are, preferably, the acid binders which are also preferred whenusing acid halides.

The reaction temperatures in the process (C-β) according to theinvention may be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C-β) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (V) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of carboxylic anhydride. Work-up is carried out bycustomary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

The process (D) is characterized in that compounds of the formula (I-a)are each reacted with chloroformic esters or chloroformic thioesters ofthe formula (VI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable acid binders for the reaction according to the process (D)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethylaniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for use in the process (D) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzine, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

When carrying out the process (D) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe process is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (D) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (D) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (VI) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed and the reaction mixture that remains isconcentrated by removing the diluent under reduced pressure.

The process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are each reacted with compounds of theformula (VII) in the presence of a diluent and, if appropriate, in thepresence of an acid binder.

In preparation process (E), about 1 mol of chloromonothioformic ester orchlorodithioformic ester of the formula (VII) is employed per mole ofthe starting material of the formula (I-a) at from 0 to 120° C.,preferably from 20 to 60° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, andalso halogenated alkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases; sodium hydroxide, sodium carbonate, potassium carbonate, pyridineand triethylamine may be mentioned by way of example.

The reaction may be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are each reacted with sulphonyl chloridesof the formula (VIII), if appropriate in the presence of a diluent andif appropriate in the presence of an acid binder.

In preparation process (F), about 1 mol of sulphonyl chloride of theformula (VIII) is reacted per mole of the starting material of theformula (I-a) at from −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction may be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (G) according to the invention is characterized in thatcompounds of the formula (I-a) are each reacted with phosphoruscompounds of the formula (IX), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (G), to obtain compounds of the formula (I-e),from 1 to 2, preferably from 1 to 1.3, mol of the phosphorus compound ofthe formula (IX) are reacted per mole of the compound (I-a), attemperatures between −40° C. and 150° C., preferably between −10 and110° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethyl-formamide, methylene chloride.

Suitable acid binders which are added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Theend products are preferably purified by crystallization, chromatographicpurification or “incipient distillation”, i.e. removal of the volatilecomponents under reduced pressure.

The process (H) is characterized in that compounds of the formula (I-a)are reacted with metal hydroxides or metal alkoxides of the formula (X)or amines of the formula (XI), if appropriate in the presence of adiluent.

Suitable diluents for use in the process (H) according to the inventionare, preferably, ethers, such as tetrahydrofuran, dioxane, diethylether, or else alcohols, such as methanol, ethanol, isopropanol, andalso water.

The process (H) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (I) according to the invention is characterized in thatcompounds of the formula (I-a) are each reacted with (I-α) compounds ofthe formula (XII), if appropriate in the presence of a diluent and ifappropriate in the presence of a catalyst, or (I-β) with compounds ofthe formula (XIII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

In preparation process (I-α), about 1 mol of isocyanate of the formula(XII) is reacted per mole of starting material of the formula (I-a), atfrom 0 to 100° C., preferably from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as ethers, amides, nitriles, sulphones or sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Suitable for use as catalysts are, very advantageously, organotincompounds, such as, for example, dibutyltin dilaurate. The reaction ispreferably carried out at atmospheric pressure.

In preparation process (I-β), about 1 mol of carbamoyl chloride of theformula (XIII) is reacted per mole of starting compound of the formula(I-a), at from −20 to 150° C., preferably at from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides orhalogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The active compounds of the invention, in combination with good planttolerance and favourable toxicity to warm-blooded animals and beingtolerated well by the environment, are suitable for protecting plantsand plant organs, for increasing the harvest yields, for improving thequality of the harvested material and for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inforests, in gardens and leisure facilities, in the protection of storedproducts and of materials, and in the hygiene sector. They may bepreferably employed as crop protection agents. They are active againstnormally sensitive and resistant species and against all or some stagesof development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.,Odontotermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active compound, synthetic materialsimpregnated with active compound, fertilizers and microencapsulations inpolymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable plants or else before or during theapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

Suitable solid carriers are:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or -POP ethers, acidand/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/orPOP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- orarylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulphonicacid derivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulphonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

The formulations generally comprise between 0.01 and 98% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be used in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances, herbicides,safeners, fertilizers or semiochemicals.

Particularly favourable mixing components are, for example, thefollowing compounds:

Fungicides:

Inhibitors of nucleic acid synthesis

-   -   benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,        dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl,        metalaxyl-M, ofurace, oxadixyl, oxolinic acid        Inhibitors of mitosis and cell division    -   benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron,        thiabendazole, thiophanate-methyl, zoxamide        Inhibitors of respiratory chain complex I    -   diflumetorim        Inhibitors of respiratory chain complex II    -   boscalid, carboxin, fenfuram, flutolanil, furametpyr, mepronil,        oxycarboxin, penthiopyrad, thifluzamide        Inhibitors of respiratory chain complex III    -   azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone,        fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,        orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin        Decouplers    -   dinocap, fluazinam        Inhibitors of ATP production    -   fentin acetate, fentin chloride, fentin hydroxide, silthiofam        Inhibitors of amino acid biosynthesis and protein biosynthesis    -   andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin        hydrochloride hydrate, mepanipyrim, pyrimethanil        Inhibitors of signal transduction    -   fenpiclonil, fludioxonil, quinoxyfen        Inhibitors of lipid and membrane synthesis    -   chlozolinate, iprodione, procymidone, vinclozolin    -   ampropylfos, potassium-ampropylfos, edifenphos, iprobenfos        (IBP), isoprothiolane, pyrazophos    -   tolclofos-methyl, biphenyl    -   iodocarb, propamocarb, propamocarb hydrochloride        Inhibitors of ergosterol biosynthesis    -   fenhexamid,    -   azaconazole, bitertanol, bromuconazole, cyproconazole,        diclobutrazole, difenoconazole, diniconazole, diniconazole-M,        epoxiconazole, etaconazole, fenbuconazole, fluquinconazole,        flusilazole, flutriafol, furconazole, furconazole-cis,        hexaconazole, imibenconazole, ipconazole, metconazole,        myclobutanil, paclobutrazole, penconazole, propiconazole,        prothioconazole, simeconazole, tebuconazole, tetraconazole,        triadimefon, triadimenol, triticonazole, uniconazole,        voriconazole, imazalil, imazalil sulphate, oxpoconazole,        fenarimol, flurprimidole, nuarimol, pyrifenox, triforine,        pefurazoate, prochloraz, triflumizole, viniconazole,    -   aldimorph, dodemorph, dodemorph acetate, fenpropimorph,        tridemorph, fenpropidin, spiroxamine,    -   naftifine, pyributicarb, terbinafine        Inhibitors of cell wall synthesis    -   benthiavalicarb, bialaphos, dimethomorph, flumorph,        iprovalicarb, polyoxins, polyoxorim, validamycin A        Inhibitors of melanin biosynthesis    -   capropamid, diclocymet, fenoxanil, phthalid, pyroquilon,        tricyclazole        Resistance inductors    -   acibenzolar-S-methyl, probenazole, tiadinil        Multisite    -   captafol, captan, chlorothalonil, copper salts such as: copper        hydroxide, copper naphthenate, copper oxychloride, copper        sulphate, copper oxide, oxine-copper and Bordeaux mixture,        dichlofluanid, dithianon, dodine, dodine free base, ferbam,        folpet, fluorofolpet, guazatine, guazatine acetate,        iminoctadine, iminoctadine albesilate, iminoctadine triacetate,        mancopper, mancozeb, maneb, metiram, metiram zinc, propineb,        sulphur and sulphur preparations containing calcium        polysulphide, thiram, tolylfluanid, zineb, ziram        Unknown mechanism    -   amibromdol, benthiazole, bethoxazin, capsimycin, carvone,        chinomethionat, chloropicrin, cufraneb, cyflufenamid, cymoxanil,        dazomet, debacarb, diclomezine, dichlorophen, dicloran,        difenzoquat, difenzoquat methyl sulphate, diphenylamine,        ethaboxam, ferimzone, flumetover, flusulphamide, fluopicolide,        fluoroimide, hexachlorobenzene, 8-hydroxy-quinoline sulphate,        irumamycin, methasulphocarb, metrafenone, methyl isothiocyanate,        mildiomycin, natamycin, nickel dimethyl dithiocarbamate,        nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin,        pentachlorophenol and salts, 2-phenylphenol and salts,        piperalin, propanosine-sodium, proquinazid, pyrrolnitrin,        quintozene, tecloftalam, tecnazene, triazoxide, trichlamide,        zarilamid and 2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine,        N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulphonamide,        2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,        2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridine-carboxamide,        3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,        cis-1-(4-chloro-phenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,        2,4-dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]phenyl]-3H-1,2,3-triazol-3-one        (185336-79-2), methyl        1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,        3,4,5-trichloro-2,6-pyridinedicarbonitrile, methyl        2-[[[cyclopropyl[(4-methoxy-phenyl)imino]methyl]thio]methyl]-.alpha.-(methoxymethylene)benzacetate,        4-chloro-alpha-propynyloxy-N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]benzacetamide,        (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphon-yl)amino]butanamide,        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]-triazolo[1,5-a]pyrimidine,        5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        5-chloro-N4[1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,        N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,        N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloro-nicotinamide,        2-butoxy-6-iodo-3-propylbenzopyranon-4-one,        N-{(Z)-[(cyclopropylmethoxy)-imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-benzacetamide,        N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide,        2-[[[[1-[3-(1-fluoro-2-phenyl-ethyl)oxy]phenyl]ethylidene]amino]oxy]methyl]alpha-(methoxyimino)-N-methyl-alphaE-benzacetamide,        N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoro-methyl)benzamide,        N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,        N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide,        1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl-1H-imidazole-1-carboxylic        acid,        O-[1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-1H-imidazole-1-carbothioic        acid,        2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methyl-acetamide        Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

Acetylcholine esterase (AChE) inhibitors

-   -   carbamates,    -   for example alanycarb, aldicarb, aldoxycarb, allyxycarb,        aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb,        butocarboxim, butoxycarboxim, carbaryl, carbofuran,        carbosulphan, cloethocarb, dimetilan, ethiofencarb, fenobucarb,        fenothiocarb, formetanate, furathiocarb, isoprocarb,        metam-sodium, methiocarb, methomyl, metolcarb, oxamyl,        pirimicarb, promecarb, propoxur, thiodicarb, thiofanox,        trimethacarb, XMC, xylylcarb, triazamate    -   organophosphates,    -   for example acephate, azamethiphos, azinphos (-methyl, -ethyl),        bromophos-ethyl, bromfenvinfos (-methyl), butathiofos,        cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos,        chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos,        cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl,        demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion,        dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,        dioxabenzofos, disulphoton, EPN, ethion, ethoprophos, etrimfos,        famphur, fenamiphos, fenitrothion, fensulphothion, fenthion,        flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate,        heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos,        isopropyl O-salicylate, isoxathion, malathion, mecarbam,        methacrifos, methamidophos, methidathion, mevinphos,        monocrotophos, naled, omethoate, oxydemeton-methyl, parathion        (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet,        phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl),        profenofos, propaphos, propetamphos, prothiofos, prothoate,        pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos,        sulphotep, sulprofos, tebupirimfos, temephos, terbufos,        tetrachlorvinphos, thiometon, triazophos, triclorfon,        vamidothion        Sodium channel modulators/voltage-dependent sodium channel        blockers    -   pyrethroids,    -   for example acrinathrin, allethrin (d-cis-trans, d-trans),        beta-cyfluthrin, bifenthrin, bioallethrin,        bioallethrin-S-cyclopentyl isomer, bioethanomethrin,        biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin,        cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin,        cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-,        zeta-), cyphenothrin, deltamethrin, empenthrin (1R isomer),        esfenvalerate, etofenprox, fenfluthrin, fenpropathrin,        fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate,        flufenprox, flumethrin, fluvalinate, fubfenprox,        gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin,        metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans        isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin,        resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin,        terallethrin, tetramethrin (1R isomer), tralomethrin,        transfluthrin, ZXI 8901, pyrethrins (pyrethrum)    -   DDT    -   oxadiazines,    -   for example indoxacarb    -   semicarbazones,    -   for example metaflumizone (BAS3201)        Acetylcholine receptor agonists/antagonists    -   chloronicotinyls,    -   for example acetamiprid, clothianidin, dinotefuran,        imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam    -   nicotine, bensultap, cartap        Acetylcholine receptor modulators    -   spinosyns,    -   for example spinosad        GABA-controlled chloride channel antagonists    -   organochlorines,    -   for example camphechlor, chlordane, endosulphan, gamma-HCH, HCH,        heptachlor, lindane, methoxychlor    -   fiprols,    -   for example acetoprole, ethiprole, fipronil, pyrafluprole,        pyriprole, vaniliprole        Chloride channel activators    -   mectins,    -   for example avermectin, emamectin, emamectin-benzoate,        ivermectin, lepimectin, milbemycin        Juvenile hormone mimetics,    -   for example diofenolan, epofenonane, fenoxycarb, hydroprene,        kinoprene, methoprene, pyriproxifen, triprene        Ecdysone agonists/disruptors    -   diacylhydrazines,    -   for example chromafenozide, halofenozide, methoxyfenozide,        tebufenozide        Chitin biosynthesis inhibitors    -   benzoylureas,    -   for example bistrifluron, chlofluazuron, diflubenzuron,        fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,        novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron    -   buprofezin    -   cyromazine        Oxidative phosphorylation inhibitors, ATP disruptors    -   diafenthiuron    -   organotin compounds,    -   for example azocyclotin, cyhexatin, fenbutatin-oxide        Oxidative phosphorylation decouplers acting by interrupting the        H-proton gradient    -   pyrroles,    -   for example chlorfenapyr    -   dinitrophenols,    -   for example binapacyrl, dinobuton, dinocap, DNOC,        Site-I electron transport inhibitors    -   METI's,    -   for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben,        tebufenpyrad, tolfenpyrad    -   hydramethylnon    -   dicofol        Site-II electron transport inhibitors    -   rotenone        Site-III electron transport inhibitors    -   acequinocyl, fluacrypyrim        Microbial disruptors of the insect gut membrane    -   Bacillus thuringiensis strains        Lipid synthesis inhibitors    -   tetronic acids,    -   for example spirodiclofen, spiromesifen    -   tetramic acids,    -   for example spirotetramate,        Carboxamides,    -   for example flonicamid        Octopaminergic agonists,    -   for example amitraz        Inhibitors of magnesium-stimulated ATPase,    -   propargite        Ryanodine receptor agonists,        (a) benzodicarboxamides,    -   for example flubendiamide        (b) anthranilamides,    -   for example rynaxypyr        (3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]-phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide)        Nereistoxin analogues,    -   for example thiocyclam hydrogen oxalate, thiosultap-sodium        Biologicals, hormones or pheromones    -   azadirachtin, Bacillus spec., Beauveria spec., codlemone,        Metarrhizium spec., Paecilomyces spec., thuringiensin,        Verticillium spec.        Active compounds with unknown or unspecific mechanisms of action    -   fumigants,    -   for example aluminium phosphide, methyl bromide, sulphuryl        fluoride    -   antifeedants,    -   for example cryolite, flonicamid, pymetrozine    -   mite growth inhibitors,    -   for example clofentezine, etoxazole, hexythiazox    -   amidoflumet, benclothiaz, benzoximate, bifenazate,        bromopropylate, buprofezin, chinomethionat, chlordimeform,        chlorobenzilate, chloropicrin, clothiazoben, cycloprene,        cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubenzimine,        flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure,        metoxadiazone, petroleum, piperonyl butoxide, potassium oleate,        pyridalyl, sulphluramid, tetradifon, tetrasul, triarathene,        verbutin

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the environment of the plant, on the surface ofparts of plants or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.00000001 to95% by weight of active compound, preferably between 0.00001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars (obtained by geneticengineering) which are to be treated according to the invention includeall plants which, by virtue of the genetic modification, receivedgenetic material which imparts particular advantageous, useful traits tothese plants. Examples of such traits are better plant growth, increasedtolerance to high or low temperatures, increased tolerance to drought orto water or soil salt content, increased flowering performance, easierharvesting, accelerated maturation, higher harvest yields, higherquality and/or a higher nutritional value of the harvested products,better storage stability and/or processability of the harvestedproducts. Further and particularly emphasized examples of such traitsare a better defence of the plants against animal and microbial pests,such as against insects, mites, phytopathogenic fungi, bacteria and/orviruses, and also increased tolerance of the plants to certainherbicidally active compounds. Examples of transgenic plants which maybe mentioned are the important crop plants, such as cereals (wheat,rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and othervegetable varieties, cotton, tobacco, oilseed rape and also fruit plants(with the fruits apples, pears, citrus fruits and grapes), andparticular emphasis is given to maize, soya beans, potatoes, cotton,tobacco and oilseed rape. Traits that are emphasized are in particularincreased defense of the plants against insects, arachnids, nematodesand slugs and snails by virtue of toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIEB2, Cry9c, Cry2Ab, Cry3Bb and CryIFand also combinations thereof) (referred to hereinbelow as “Bt plants”).Traits that are also particularly emphasized are the increased defenceof plants against fungi, bacteria and viruses by systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and resistance genesand correspondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance ofplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these genetic traits orgenetic traits still to be developed, which plant cultivars will bedeveloped and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula I and/or the active compound mixtures according to theinvention. The preferred ranges stated above for the active compounds ormixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ecto- and endoparasites), suchas hard ticks, soft ticks, mange mites, leaf mites, flies (biting andlicking), parasitic fly larvae, lice, hair lice, feather lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reductions in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector and in animal husbandry in a known manner by enteraladministration in the form of, for example, tablets, capsules, potions,drenches, granules, pastes, boluses, the feed-through process andsuppositories, by parenteral administration, such as, for example, byinjection (intramuscular, subcutaneous, intravenous, intraperitoneal andthe like), implants, by nasal administration, by dermal use in the form,for example, of dipping or bathing, spraying, pouring on and spottingon, washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100- to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout any limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctis pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. Dinoderus minutus;

Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cardboards, leather, wood and processed wood productsand coating compositions.

The ready-to-use compositions may, if appropriate, comprise furtherinsecticides and, if appropriate, one or more fungicides.

With respect to possible additional additives, reference may be made tothe insecticides and fungicides mentioned above.

The compounds according to the invention can likewise be employed forprotecting objects which come into contact with saltwater or brackishwater, in particular hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Furthermore, the compounds according to the invention, alone or incombinations with other active compounds, may be employed as antifoulingagents.

In domestic, hygiene and stored-product protection, the active compoundsare also suitable for controlling animal pests, in particular insects,arachnids and mites, which are found in enclosed spaces such as, forexample, dwellings, factory halls, offices, vehicle cabins and the like.They can be employed alone or in combination with other active compoundsand auxiliaries in domestic insecticide products for controlling thesepests. They are active against sensitive and resistant species andagainst all developmental stages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber. From the order of the Diplopoda, for example, Blaniulusguttulatus, Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricesters, carbamates, pyrethroids, neonicotinoids, growth regulators oractive compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds/active compound combinations according to theinvention can also be used as defoliants, desiccants, haulm killers and,in particular, as weed killers. Weeds in the broadest sense areunderstood as meaning all plants which grow at locations where they areundesired. Whether the substances according to the invention act asnonselective or selective herbicides depends essentially on theapplication rate.

The active compounds/active compound combinations according to theinvention can be used for example in the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds/active compound combinationsaccording to the invention is in no way restricted to these genera, butextends in the same manner to other plants.

Depending on the concentration, the active compounds/active compoundcombinations according to the invention are suitable for thenonselective weed control on, for example, industrial terrains andrailway tracks and on paths and locations with and without trees.Likewise the active compounds according to the invention can be employedfor controlling weeds in perennial crops, for example forests,ornamental tree plantings, orchards, vineyards, citrus groves, nutorchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hop fields, on lawns, turf and pastureland, and for theselective control of weeds in annual crops.

The compounds of the formula (I)/active compound combinations accordingto the invention have strong herbicidal activity and a broad activityspectrum when used on the soil and on aerial plant parts. To a certainextent, they are also suitable for the selective control ofmonocotyledonous and dicotyledonous weeds in monocotyledonous anddicotyledonous crops, both pre- and post-emergence.

At certain concentrations or application rates, the activecompounds/active compound combinations according to the invention canalso be employed for controlling animal pests and fungal or bacterialplant diseases. If appropriate, they can also be used as intermediatesor precursors for the synthesis of other active compounds.

The active compounds/active compound combinations can be converted intothe customary formulations, such as solutions, emulsions, wettablepowders, suspensions, powders, dusts, pastes, soluble powders, granules,suspoemulsion concentrates, natural and synthetic materials impregnatedwith active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics, such as xylene, toluene or alkyl-naphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols, such as butanol orglycol, and also their ethers and esters, ketones, such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents, such as dimethylformamide and dimethyl sulphoxide, andalso water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates, suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,and also synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam-formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalo-cyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds/active compound combinations according to theinvention, as such or in their formulations, can also be used for weedcontrol purposes as a mixture with known herbicides and/or withsubstances which improve crop plant tolerance (“safeners”), ready mixesor tank mixes being possible. Mixtures with herbicide products whichcontain one or more known herbicides and a safener are hence alsopossible.

Herbicides which are suitable for the mixtures are known herbicides, forexample

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulphuron,aminopyralid, anilofos, asulam, atrazine, azafenidin, azimsulfuron,beflubutamid, benazolin (-ethyl), bencarbazone, benfuresate, bensulfuron(-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap,benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl),butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl),cinmethylin, cinosulphuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulphuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulphuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, HOK-201, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, KIH 485, lactofen, lenacil, linuron, MCPA,mecoprop, mefenacet, mesosulfurone, mesotrione, metamifop, metamitron,metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl),molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron,norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, penoxsulam, pentoxazone,phenmedipham, picolinafen, pinoxaden, piperophos, pretilachlor,primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil,propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide,prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrasulfotole,pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen,pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalide,pyriminobac (-methyl), pyrimisulfan, pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tembotrione,tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb,tiocarbazil, topramezone, tralkoxydim, triallate, triasulfuron,tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulphuron, triflusulfuron (-methyl), tritosulfuron and

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand soil conditioners, is also possible.

The active compounds or active compound combinations can be applied assuch, in the form of their formulations or the use forms preparedtherefrom by further dilution, such as ready-to-use solutions,suspensions, emulsions, powders, pastes and granules. They are appliedin the customary manner, for example by watering, spraying, atomizing,spreading.

The active compounds or active compound combinations according to theinvention can be applied both before and after plant emergence. They canalso be incorporated into the soil prior to planting.

The application rate of active compound can vary within a substantialrange. Essentially, it depends on the nature of the desired effect. Ingeneral, the application rates are between 1 g and 10 kg of activecompound per hectare of soil area, preferably between 5 g and 5 kg perha.

The advantageous effect of the compatibility with crop plants of theactive compound combinations according to the invention is particularlypronounced at certain concentration ratios.

However, the weight ratios of the active compounds in the activecompound combinations can be varied within relatively wide ranges. Ingeneral, from 0.001 to 1000 parts by weight, preferably from 0.01 to 100parts by weight, particularly preferably 0.05 to 20 parts by weight, ofone of the compounds which improves crop plant compatibility(antidotes/safeners) mentioned above under (b′) are present per part byweight of active compound of the formula (I).

The active compound combinations according to the invention aregenerally applied in the form of finished formulations. However, theactive compounds contained in the active compound combinations can, asindividual formulations, also be mixed during use, i.e. be applied inthe form of tank mixes.

For certain applications, in particular by the post-emergence method, itmay furthermore be advantageous to include, as further additives in theformulations, mineral or vegetable oils which are tolerated by plants(for example the commercial preparation “Rako Binol”), or ammoniumsalts, such as, for example, ammonium sulphate or ammonium thiocyanate.

The novel active compound combinations can be used as such, in the formof their formulations or the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. Application is in the customary manner,for example by watering, spraying, atomizing, dusting or scattering.

The application rates of the active compound combinations according tothe invention can be varied within a certain range; they depend, interalia, on the weather and on soil factors. In general, the applicationrates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.

The active compound combinations according to the invention can beapplied before and after emergence of the plants, that is to say by thepre-emergence and post-emergence method.

Depending on their properties, the safeners to be used according to theinvention can be used for pretreating the seed of the crop plant (seeddressing) or can be introduced into the seed furrows prior to sowing orbe used separately prior to the herbicide or together with theherbicide, before or after emergence of the plants.

The term “active compounds” also includes the active compoundcombinations mentioned.

Preparation and use of the active compounds according to the inventionis illustrated by the examples below.

EXAMPLE (I-a-1)

At 40-50° C., 7.3 g of the compound of Example II-1 inN,N-dimethylacetamide are added dropwise to 4.59 g (38.8 mmol) ofpotassium tert-butoxide in 10 ml of dimethylacetamide, and the mixtureis stirred at 50° C. for 3 hours.

After having been checked by thin-layer chromatography, the reactionmixture is poured into 200 ml of ice-water and, at 0-10° C., adjusted topH 4 using 1N hydrochloric acid. The precipitate is filtered off withsuction, washed and dried.

Yield: 4.45 g (63% of theory), m.p. 210° C.

EXAMPLE (I-a-3)

0.76 g (2 mmol) of the compound of Ex. I-5 from WO 01/89300, 0.52 g (3mmol) of 3,4,5-trifluorophenylboronic acid and 1.06 g (10 mmol) ofsodium carbonate are initially charged in 15 ml of water. 0.05 g (0.2mmol) of palladium(II) nitrate dihydrate is added, and the mixture isheated under reflux at 120° C. for 8 h. The reaction mixture is thenacidified with dilute hydrochloric acid, and the precipitate is filteredoff with suction. Purification is carried out by MPLC on silica gelusing cyclohexane/acetone 7:3.

Yield: 0.37 g (40% of theory), m.p. 277° C.

Analogously to Example (I-a-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-a) are obtained

(I-a)

Ex. No. W X Y F V¹ V² A m.p. °C. I-a-2 CH₃ CH₃ H 4 H H CH₃ 226 I-a-3 CH₃CH₃ H 4 3-F 5-F CH₃ 277 I-a-4 CH₃ CH₃ H 4 3-F H CH₃ 288 I-a-5 CH₃ CH₃CH₃ 4 H H CH₃ 290 I-a-6 CH₃ CH₃ H 4 3-Cl H CH₃ — I-a-7 CH₃ CH₃ H 43-OCH₃ H CH₃ — I-a-8 CH₃ CH₃ H 3 H H CH₃ 260 I-a-9 H Cl H 4 H H CH₃ 122I-a-10 H Cl H 4 H H C₂H₅ 113 I-a-11 CH₃ CH₃ H 4 H H C₂H₅ 274 I-a-12 HCH₃ H 4 H H C₂H₅ 158 I-a-13 H CH₃ H 4 3-F H CH₃ 245 I-a-14 H CH₃ H 43-Cl H CH₃ 250

EXAMPLE I-b-1

0.21 ml of triethylamine and 10 mg of 4-N,N-dimethylaminopyridine areadded to 0.57 g (1.5 mmol) of the compound of Example I-a-1 in 20 ml ofethyl acetate. Under reflux, 0.12 ml (1.5 mmol) of acetyl chloride in 1ml of ethyl acetate is added dropwise, and the mixture is stirred underreflux for one hour. The solvent is removed under reduced pressure usinga rotary evaporator, and the residue is purified on silica gel usingdichloromethane/ethyl acetate (gradient from 10:1 to 3:1).

Yield: 0.55 g (^ 75% of theory), m.p. 206° C.

Analogously to Example (I-b-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-b) are obtained

(I-b)

Ex. No. W X Y F V¹ V² A R¹ m.p. °C. I-b-2 H CH₃ H 4 H H CH₃ i-C₃H₇ 174I-b-3 CH₃ CH₃ H 4 H H CH₃ i-C₃H₇ 227 I-b-4 CH₃ CH₃ H 4 H H CH₃ CH₃ 212I-b-5 CH₃ CH₃ H 4 H H CH₃

69

EXAMPLE I-c-1

0.21 ml of triethylamine and 10 mg of 4-N,N-dimethylaminopyridine areadded to 0.57 g (1.5 mmol) of the compound of Example I-a-1 in 20 ml ofdichloromethane. At 20° C., 0.14 ml (1.5 mmol) of ethyl chloroformate indichloromethane is added dropwise, and the mixture is stirred at roomtemperature for one hour. The solvent is removed under reduced pressureusing a rotary evaporator, and the residue is purified on silica gelusing dichloromethane/ethyl acetate(10:1).

Yield: 0.6 g (^ 88% of theory), m.p. 193° C.

Analogously to Example (I-c-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(I-c) are obtained

Ex. No. W X Y F V¹ V² A M R² m.p. °C. I-c-2 CH₃ CH₃ H 4 H H CH₃ O C₂H₅174 I-c-3 CH₃ CH₃ H 4 H H CH₃ O CH₃ 192 I-c-4 H CH₃ H 4 H H CH₃ O CH₃242

EXAMPLE (I-f-1)

A little at a time, 0.39 g (1 mmol) of the compound of Example (I-a-2)is introduced into a solution of 5 ml of water and 1 ml of 1N aqueoussodium hydroxide solution, and the mixture is stirred at 20° C. for 1 hand concentrated using a rotary evaporator.

Yield: quantitative

¹H-NMR (400 MHz, d6-DMSO): =2.01, 2.06 (2s, 3H each, Ar—CH ₃), 3.25 (s,3H, OCH ₃), 6.75 (d, 1H, Ar—H), 6.89-6.90 (d, 1H, Ar—H), 7.13-7.19 (m,2H, Ar—H), 7.22-7.26 (m, 2H, Ar—H) ppm.

Analogously to Example (I-f-1), Example (I-f-2) is obtained

¹H-NMR (400 MHz, d₆-DMSO): δ=2.22 (s, 3H, Ar—CH ₃), 3.25 (s, 3H, OCH₃),7.02-7.08 (m, 2H, Ar—H), 7.15-7.21 (m, 2H, Ar—H), 7.51-7.58 (m, 3H,Ar—H) ppm.

EXAMPLE II-1

4.9 g (20 mmol) of 3-(4-fluorophenyl)-6-methylphenylacetic acid and 7.3ml of thionyl chloride are heated at 80° C. until the evolution of gashas ended. Excess thionyl chloride is removed at 50° C. under reducedpressure, and the residue is taken up in 50 ml of ethyl acetate(solution 1).

4.92 g (22 mmol) of methyl cis-4-methoxy-1-aminocyclohexanecarboxylatehydrochloride are initially charged in 50 ml of ethyl acetate, and 22 mlof 1N aqueous sodium hydroxide solution are added dropwise at 0-5° C.Solution 1 and a further 20 ml of 1N sodium hydroxide solution are thensimultaneously added dropwise at 0-5° C. After the reaction has ended(according to thin-layer chromatography), the mixture is extracted withethyl acetate, the extract is dried and concentrated under reducedpressure using a rotary evaporator and the residue is chromatographed onsilica using the mobile phase methylene chloride/ethyl acetate.

Yield: 7.4 g (=84% of theory), m.p. 126° C.

Analogously to Example (II-1) and in accordance with the generalstatements on the preparation, the following compounds of the formula(II) are obtained

Ex. No. W X Y F V¹ V² A R⁸ m.p. °C. II-2 CH₃ CH₃ H 4 H H CH₃ CH₃ 165II-3 CH₃ CH₃ CH₃ 4 H H CH₃ CH₃ 198 II-4 H Cl H 4 H H CH₃ CH₃ * 3.23 (s,3H, OCH ₃) 3.53 (s, 3H, CO₂ CH ₃) 3.71 (s, 2H, CO—CH ₂) 7.24-7.29 (m,2H, Ar—H)) II-5 CH₃ CH₃ H 4 H H C₂H₅ CH₃ * 1.09 (t, 3H, CH₂, CH ₃) 2.10,2.48 (2s, 3H each, ArCH ₃) 3.45(a, 2H, O—CH ₂CH₃) 3.52 (s, 3H, CO₂, CH₃) 3.66 (s, 2H, COCH ₂) II-6 H Cl H 4 H H C₂H₅ CH₃ * 1.09 (t, 3H, CH₂ CH₃) 3.26 (m, 1H, OCH) 3.44 (a, 2H, O—CH ₂) 3.52 (s, 3H, CO₂ CH ₃) 3.71(s, 2H, CO—CH ₂) II-7 H CH₃ H 4 H H C₂H₅ CH₃ * 1.08 (t, 3H, CH₂—CH ₃)2.28 (s, 3H, ArCH ₃) 3.43 (a, 2H, COCH ₂) 3.57 (s, 2H, COCH ₂) 7.60-7.64(m, 2H, ArH)

EXAMPLE 1 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium saltsor phosphonium salts these are added in a concentration of 1000 ppm tothe spray liquor.

Cotton plants (Gossypium hirsutum) which are severely infested withcotton aphids (Aphis gossypii) are treated by spraying to runoff pointwith the preparation of the active substance at the desiredconcentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

TABLE 1 Active Active compound Kill rate/% after 6 days compoundconcentration/ppm +AS (1000 ppm) I-a-2 20 15 25 I-a-5 100 40 65

EXAMPLE 2 Activity Boost Through Ammonium/Phosphonium Salts inCombination with Penetrants

Myzus persicae Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. For application with ammonium salts or phosphonium saltsand penetrants (rapeseed oil methyl ester 500 EW) these are added ineach case in a concentration of 1000 ppm to the spray liquor.

Bell pepper plants (Capsicum annuum) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated with the active compoundpreparation of the desired concentration by spraying to runoff point.After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

TABLE 2 Kill rate/% after 6 days Active Active compound +AS +RME +RME +AS compound concentration/ppm (1000 ppm) (1000 ppm) (1000 ppm each)I-a-1 0.8 10 0 30 70

EXAMPLE 3 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium saltsor phosphonium salts and penetrant (rapeseed oil methyl ester 500 EW)these are added in each case in a concentration of 1000 ppm (a.i.) tothe spray liquor.

Cotton plants (Gossypium hirsutum) which are heavily infested by thecotton aphid (Aphis gossypii) are treated with the active compoundpreparation of the desired concentration by spraying to runoff point.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

TABLE 3 Kill rate/% after 6 days Active Active compound +AS +RME +RME +AS compound concentration/ppm (1000 ppm) (1000 ppm) (1000 ppm each)I-a-1 20 5 15 70 80 I-a-5 20 0 25 15 65

EXAMPLE 4 Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood fibre pots and covered with soil. The testcompounds, formulated in the form of wettable powders (WP), are then, asan aqueous suspension with a water application rate of 600 l/ha(converted) with 0.2% of wetting agent added, applied at various dosagesto the surface of the covering soil.

After the treatment, the pots are placed in a greenhouse and kept undergood growth conditions for the test plants. The visual assessment of theemergence damage on the test plants is carried out after a trial periodof 3 weeks by comparison with the untreated control (herbicidal activityin %: 100% activity=the plants have died, 0% activity=like controlplants).

In addition to the compounds mentioned above, the following compounds,applied by the pre-emergence method at 320 g/ha of a.i./ha, show anactivity of ≧80% against Echinocloa crus-galli, Lolium multiflorum andSetaria viridis: I-a-2, I-a-3, I-a-4, I-b-1, I-b-2, I-b-3, I-b-4, I-c-1,I-c-2, I-c-3, I-c-4.

EXAMPLE 5 Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood fibre pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thetest compounds, formulated as wettable powders (WP), are then, invarious dosages with a water application rate of 600 l/ha (converted),with 0.2% of wetting agent added, sprayed onto the green parts of theplants. After the test plants have been kept in the greenhouse underoptimum growth conditions for about 3 weeks, the effect of thepreparations is rated visually in comparison to untreated controls(herbicidal activity in per cent: 100% activity=the plants have died, 0%activity=like control plants).

In addition to the compounds mentioned above, the following compounds,applied by the post-emergence method at 80 g/ha, show an activity of≧80% against Echinocloa crus-galli and Setaria viridis: I-a-1, I-a-2,I-b-1, I-b-2, I-c-3.

EXAMPLE 6 Myzus Test (MYZUPE Spray Treatment)

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of chinese cabbage (Brassica pekinensis) which are infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After the desired period of time, the effect in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an activity of ≧80%:

Example Nos. I-a-1, I-a-2, I-a-3, I-a-4, I-a-5, I-a-6, I-a-7, I-a-8,I-b-1, I-b-2, I-b-3, I-b-4, I-c-1, I-c-2, I-c-3, I-c-4.

EXAMPLE 7 Phaedon Test (PHAECO Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of chinese cabbage (Brassica pekinensis) are sprayed with anactive compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired period of time, the effect in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an activity of ≧80%:

Example Nos. I-a-3, I-a-4, I-a-5, I-a-6, I-a-7, I-a-8

EXAMPLE 8 Spodoptera frugiperda Test (SPODFR Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of maize leaves (Zea mays) are sprayed with an active compoundpreparation of the desired concentration and, after drying, populatedwith caterpillars of the army worm (Spodoptera frugiperda).

After the desired period of time, the effect in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an activity of ≧80%:

Example Nos. I-a-1, I-a-2, I-a-3, I-a-4, I-a-5, I-b-1, I-b-2, I-b-3,I-b-4, I-c-1, I-c-2, I-c-3, I-c-4.

EXAMPLE 9 Tetranychus Test, OP-Resistant (TETRUR Spray Treatment)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of bean leaves (Phaseolus vulgaris) which are infested by allstages of the greenhouse red spidermite (Tetranychus urticae) aresprayed with an active compound preparation of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all spidermites have been killed; 0% means that none of thespidermites have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 g/ha, an activity of ≧80%:

Example Nos. I-a-3, I-c-2

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an activity of >80%:

Example Nos. I-a-1, I-a-2, I-b-1, I-b-2, I-b-3, I-b-4, I-c-1, I-c-3,I-c-4

EXAMPLE 10 Aphis gossypii Test; (APHIGO G)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cotton plants (Gossypium hirsutum) which are heavily infested by thecotton aphid (Aphis gossypii) are watered with an active compoundprepartion of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 ppm, an activity of ≧80%after 10 days:

Example Nos. I-a-3, I-a-5, I-b-4, I-c-2, I-c-3

EXAMPLE 11 Myzus persicae Test; (MYZUPE G)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage plants (Brassica oleracea) which are heavily infested by thegreen peach aphid (Myzus persicae) are watered with an active compoundprepartion of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 ppm, an activity of ≧80%after 10 days:

Example Nos. I-a-5, I-c-2, I-c-4

EXAMPLE 12 Tetranychus-Test; OP-Resistant (TETRUR G)

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by the allstages of the greenhouse red spidermite (Tetranychus urticae) arewatered with an active compound prepartion of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all spidermites have been killed; 0% means that none of thespidermites have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 ppm, an activity of ≧80%after 14 days:

Example Nos. I-a-3, I-a-5, I-b-1, I-b-2, I-b-3, I-b-4, I-c-1, I-c-2,I-c-3, I-c-4

EXAMPLE 13 Boophilus microplus Test (BOOPMI Injection)

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with solvent to the desired concentration.

The active compound solution is injected into the abdomen (Boophilusmicroplus) and the animals are transferred into dishes and stored in aclimatized room.

After the desired period of time the activity in % is determined. 100%means that none of the ticks has laid fertile eggs.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 μg/animal, an activity of≧80%:

Example Nos. I-a-1, I-a-2, I-b-1

EXAMPLE 14 Lucilia cuprina Test (LUCICU)

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of water, and theconcentrate is diluted with water to the desired concentration.

Containers containing horse meat treated with the active compoundpreparation of the desired concentration are populated with Luciliacuprina larvae.

After the desired period of time, the kill in % is determined. 100%means that all larvae have been killed; 0% means that none of the larvaehave been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 ppm, an activity of ≧80%:

Example Nos. I-a-1, I-a-2, I-b-1

EXAMPLE 15 Heliothis virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soya bean shoots (Glycine max) of the cultivar Roundup Ready (trade markof Monsanto Comp. USA) are treated by being dipped into the activecompound preparation of the desired concentration and are populated withthe tobacco bud worm Heliothis virescens while the leaves are stillmoist.

After the desired period of time, the kill of the insects is determined.

EXAMPLE 16 Critical Concentration Test/Soil Insects—Treatment ofTransgenic Plants

Test insect: Diabrotica balteata—larvae in the soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The active compound preparation is poured onto the soil Here, theconcentration of active compound in the preparation is virtuallyimmaterial; only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l) matters. The soil is filled into0.25 l pots, and these are allowed to stand at 20° C.

Immediately after the preparation, 5 pregerminated maize corns of thecultivar YIELD GUARD (trade mark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the appropriate test insects are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% activity).

The invention claimed is:
 1. A compound of formula (I),

W represents hydrogen or methyl, X represents chlorine or methyl, Y represents hydrogen or methyl, Z represents the radicals

V¹, V² independently of one another represent hydrogen, fluorine, chlorine or methoxy, A represents methyl or ethyl, G represents hydrogen (a) or represents one of the groups

in which E represents a metal ion equivalent (Na⁺), R¹ represents C₁-C₆-alkyl or cyclopropyl, R² represents C₁-C₈-alkyl.
 2. A process for preparing a compound of the formula (I) according to claim 1, characterized in that, to obtain (A) a compound of the formula (I-a),

a compound of the formula (II),

in which R⁸ represents alkyl, is condensed intramolecularly in the presence of a diluent and in the presence of a base, (B) a compound of the formulae (I-a) to (I-g), a compound of the formulae (I-a′) to (I-g′), respectively,

in which Z′ represents chlorine, bromine, or iodine, is reacted with a boronic acid or a boronic acid derivative of formula (III)

in which R⁹ represents hydrogen, C₁-C₆-alkyl or C₂-C₆-alkanediyl and in the presence of a diluent, a base and a catalyst, (C) a compound of the formula (I-b), a compound of the formula (I-a), is in each case (α) reacted with acid halide of formula (IV)

in which Hal represents halogen, or (β) reacted with a carboxylic anhydride of formula (V) R¹—CO—O—CO—R¹  (V) optionally in the presence of a diluent and optionally in the presence of an acid binder; (D) a compound of the formula (I-c) in which L represents oxygen, a compound of the formula (I-a), is in each case reacted with a chloroformic ester or a chloroformic thioester of formula (VI) R²-M-CO—Cl  (VI) optionally in the presence of a diluent and optionally in the presence of an acid binder; (E) a compound of the formula (I-c) in which L represents sulphur, a compound of the formula (I-a), is in each case reacted with a chloromonothioformic ester or a chlorodithioformic ester of formula (VII)

optionally in the presence of a diluent and optionally in the presence of an acid binder and (F) a compound of the formula (I-d), a compound of the formula (I-a), is in each case reacted with a sulphonyl chloride of formula (VIII) R³—SO₂—Cl  (VIII) optionally in the presence of a diluent and optionally in the presence of an acid binder, (G) a compound of the formula (I-e), a compound of the formula (I-a) is in each case reacted with a phosphorus compound of formula (IX)

in which Hal represents halogen, optionally in the presence of a diluent and optionally in the presence of an acid binder, (H) a compound of the formula (I-f), a compound of the formula (I-a), is in each case reacted with a metal compound or an amine of formulae (X) and (XI), respectively,

in which Me represents a mono- or divalent metal, t represents the number 1 or 2 and R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or alkyl, optionally in the presence of a diluent, (I) a compound of the formula (I-g), a compound of the formula (I-a), is in each case (α) reacted with an isocyanate or an isothiocyanate of formula (XII) R⁶—N═C=L  (XII) optionally in the presence of a diluent and optionally in the presence of a catalyst, or (β) reacted with a carbamoyl chloride or a thiocarbamoyl chloride of formula (XIII)

optionally in the presence of a diluent and optionally in the presence of an acid binder.
 3. A composition comprising an effective amount of an active compound combination comprising, (a′) at least one compound of the formula (I) according to claim 1, and (b′) at least one crop plant compatibility-improving compound selected from the group consisting of: 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor), 1-methylhexyl 5-chloroquinoline-8-oxyacetate(cloquintocet-mexyl), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide(dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl, phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl, 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid (AC-304415), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulphonylbenzene, 1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide, one of the following compounds, defined by general formulae general formula (IIa)

general formula (IIb)

formula (IIc)

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of the divalent heterocyclic groupings shown below

n represents a number 0, 1, 2, 3, 4 or 5, A² represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl- and/or C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbon atoms, R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄alkyl)-amino, R¹⁶ represents optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, R¹⁷ represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl, R¹⁷ and R¹⁸ also together represent C₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionally substituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl, R²⁰ represents hydrogen, in each case optionally hydroxyl-, cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl or tri(C₁-C₄-alkyl)silyl, R²¹ represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, the following compounds, defined by general formulae general formula (IId)

and general formula (He)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ represents hydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino, R²⁵ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, R²⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together with R²⁵ represents in each case optionally C₁-C₄-alkyl-substituted C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 4. A composition according to claim 3, in which the crop plant compatibility-improving compound is selected from the group consisting of: cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron and the compounds


5. A composition according to claim 3, in which the crop plant compatibility-improving compound is cloquintocet-mexyl.
 6. A composition according to claim 3, in which the crop plant compatibility-improving compound is mefenpyr-diethyl.
 7. A composition, comprising at least one compound of the formula (I) according to claim 1 and at least one salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹ independently of one another represent hydrogen or in each case optionally substituted C₁-C₈-alkyl or mono- or polyunsaturated, optionally substituted C₁-C₈-alkylene, the substituents being selectable from halogen, nitro and cyano, N represents 1, 2, 3 or 4, R³⁰ represents an organic or inorganic anion.
 8. A composition according to claim 7, further comprising at least one penetrant.
 9. A pesticide and/or herbicide, comprising at least one compound of the formula (I) according to claim
 1. 10. A method for controlling animal pests and/or unwanted vegetation, comprising contacting a compound of the formula (I) according to claim 1 with pests and/or their habitat.
 11. A process for preparing pesticides and/or herbicides, comprising mixing a compound of the formula (I) according to claim 1 with an extender, a surfactant, or a combination thereof.
 12. A method for controlling unwanted vegetation, comprising contacting a composition according to claim 3 with plants or their surroundings.
 13. A method for controlling unwanted vegetation, comprising contacting plants or their surroundings with a compound of the formula (I) according to claim 1 and a crop plant compatibility-improving compound selected from the group consisting of: 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor), 1-methylhexyl 5-chloroquinoline-8-oxyacetate(cloquintocet-mexyl), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide(dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl, phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl, 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838), 1,8-naphthalic anhydride, a-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid (AC-304415), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulphonylbenzene, 1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[methylaminocarbonyl)amino]benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulphonamide, one of the following compounds, defined by general formulae general formula (IIa)

general formula (IIb)

formula (IIc)

where m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of the divalent heterocyclic groupings shown below

n represents a number 0, 1, 2, 3, 4 or 5, A² represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxy-carbonyl- and/or C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbon atoms, R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)-amino, R¹⁶ represents optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, R¹⁷ represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen, in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine- and/or bromine- or C₁-C₄-alkyl-substituted phenyl, R¹⁷ and R¹⁸ also together represent C₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionally substituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl, R²⁰ represents hydrogen, in each case optionally hydroxyl-, cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl or tri(C₁-C₄-alkyl)silyl, R²¹ represents hydrogen, cyano, halogen, or represents in each case optionally fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, the following compounds, defined by general formulae general formula (IId)

and general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0, 1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ represents hydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino, R²⁵ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally cyano-, halogen or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, R²⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together with R²⁵ represents in each case optionally C₁-C₄-alkyl-substituted C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, and X⁵ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy separately in close temporal succession, on the plants or their surroundings. 